Shun-Jun Ji

Aqueous Reaction of Alcohols, Organohalides, and Odorless Sodium Thiosulfate under Transition-Metal-Free Conditions: Synthesis of Unsymmetrical Aryl Sulfides via Dual C–S Bond Formation

Co-reporter:Bei-Bei Liu, Xue-Qiang Chu, Huan Liu, Ling Yin, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry October 6, 2017 Volume 82(Issue 19) pp:10174-10174

Publication Date(Web):September 14, 2017

DOI:10.1021/acs.joc.7b01653

A transition-metal-free process for the synthesis of unsymmetrical aryl sulfides via dual C–S bond formation by a one-pot three-component reaction of alcohols, organohalides, and odorless sodium thiosulfate in water has been developed. In addition, the aryl sulfides could also be prepared by the reaction of the corresponding alcohols and Bunte salts under the identical conditions. This protocol provides a green and efficient manner for the construction of various unsymmetrical aryl sulfides.

Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates

Co-reporter:Huan Liu, Yi Fang, Ling Yin, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry October 20, 2017 Volume 82(Issue 20) pp:10866-10866

Publication Date(Web):September 14, 2017

DOI:10.1021/acs.joc.7b01663

A new and facile approach toward highly functionalized carbamimidoseleknoates was developed through the copper(I)-catalyzed ligand-promoted four-component reaction of isocyanides, selenium, amines, and aryl iodides. The reaction constructed a range of organoselenium compounds containing an isoselenourea skeleton with potential bioactivity directly from selenium powder. The simplicity of method and broad diversity of substrates also highlight this work.

Cobalt(II)-Catalyzed Synthesis of Sulfonyl Guanidines via Nitrene Radical Coupling with Isonitriles: A Combined Experimental and Computational Study

Co-reporter:Zheng-Yang Gu, Yuan Liu, Fei Wang, Xiaoguang Bao, Shun-Yi Wang, and Shun-Jun Ji

ACS Catalysis June 2, 2017 Volume 7(Issue 6) pp:3893-3893

Publication Date(Web):April 26, 2017

DOI:10.1021/acscatal.7b00798

A Co(II)-catalyzed synthesis of sulfonyl guanidines by using amines, isonitriles, and organic azides as nitrene sources has been developed. This protocol provides an environmentally friendly and simple strategy for the synthesis of sulfonyl guanidine derivatives by employing a range of substrates and will find potential applications in organic synthesis. The computational and EPR studies suggested the formation of guanidine derivatives via a cobalt–nitrene radical intermediate.Keywords: amines; cobalt(II)-catalysis; computational study; isonitriles; nitrene; organic azides; sulfonyl guanidines;

Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Sulfonyl Azides in Alcohols: Synthesis of Sulfonyl Isoureas

Co-reporter:Tian Jiang, Zheng-Yang Gu, Ling Yin, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry August 4, 2017 Volume 82(Issue 15) pp:7913-7913

Publication Date(Web):July 7, 2017

DOI:10.1021/acs.joc.7b01127

A Co(II)-catalyzed isocyanide insertion reaction with sulfonyl azides in alcohols to form sulfonyl isoureas via nitrene intermediate has been developed. This protocol provides a new, environmentally friendly, and simple strategy for the synthesis of sulfonyl isourea derivatives by employing a range of substrates under mild conditions.

Silver-Catalyzed Regioselective Fluorination of Carbonyl Directed Alkynes: Synthesis of α-Fluoroketones

Co-reporter:Fang-Hui Li, Zhong-Jian Cai, Ling Yin, Jian Li, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters April 7, 2017 Volume 19(Issue 7) pp:

Publication Date(Web):March 15, 2017

DOI:10.1021/acs.orglett.7b00453

A novel silver-catalyzed fluorination reaction of carbonyl directed alkynes in the presence of N-fluorobenzenesulfonimide and water with high regioselectivities has been developed. The established protocol provides an alternative method for rapid assembly of α-fluoroketone derivatives under simple and mild reaction conditions. The reaction pathway involves a ring closure and opening process for the construction of new C–O and C–F bonds. In addition, a fluorine-containing indanone was observed through further N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction of α-fluoroketone.

Cobalt-Catalyzed Annulation of Amides with Isocyanides via C(sp2)–H Activation

Co-reporter:Zheng-Yang Gu, Cheng-Guo Liu, Shun-Yi WangShun-Jun Ji

The Journal of Organic Chemistry 2017 Volume 82(Issue 4) pp:

Publication Date(Web):January 25, 2017

DOI:10.1021/acs.joc.6b02797

A cobalt-catalyzed [4 + 1] cycloaddition of easily accessible amides with isocyanides for the efficient synthesis of 3-iminoisoindolinone derivatives in high yield under mild conditions via intramolecular C(sp2)–H activation and isocyanide insertion is reported. The annulation was found to be applicable to a broad range of substrates, including arylamides, heteroarylamides, and acrylamide derivatives. Strongly coordinating N-heterocyclic directing groups such as pyridine, pyrimidine, and even pyrazole were fully tolerated in this cobalt-catalyzed C–H activation reaction.

Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

Co-reporter:Xue-Qiang Chu, Wen-Bin Cao, Xiao-Ping Xu, and Shun-Jun Ji

The Journal of Organic Chemistry 2017 Volume 82(Issue 2) pp:

Publication Date(Web):December 29, 2016

DOI:10.1021/acs.joc.6b02767

An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C–H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.

Cobalt(II)-catalyzed bis-isocyanide insertion reactions with sulfonyl azides via nitrene radicals: chemoselective synthesis of sulfonylamidyl amide and 3-imine indole derivatives

Co-reporter:Zheng-Yang Gu;Jing-Hao Li;Shun-Yi Wang

Chemical Communications 2017 vol. 53(Issue 81) pp:11173-11176

Publication Date(Web):2017/10/10

DOI:10.1039/C7CC06531K

A chemoselective Co(II)-catalyzed effective synthesis of sulfonylamidyl amide and 3-imine indole derivatives by using isocyanides and sulfonyl azides has been developed. This protocol provides a new, environmentally friendly and simple strategy for the efficient synthesis of the sulfonylamidyl amide and 3-imine indole derivatives with a wide range of substrates in the absence of any oxidants and additives.

Copper-catalyzed construction of eight-membered rings via oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines: efficient synthesis of benzo[1,3,5]triazocin-6(5H)-ones

Co-reporter:Wen-Bin Cao;Xue-Qiang Chu;Yu Zhou;Ling Yin;Xiao-Ping Xu

Chemical Communications 2017 vol. 53(Issue 49) pp:6601-6604

Publication Date(Web):2017/06/16

DOI:10.1039/C7CC02815F

Novel and efficient synthesis of eight-membered nitrogen heterocycles in one pot by copper-catalyzed oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines has been described. This protocol features easily available substrates and high step-economy. More importantly, dioxygen as the most ideal oxidant was employed under mild reaction conditions. A variety of valuable benzo[1,3,5]triazocin-6(5H)-one derivatives bearing functional groups were assembled in middle to good yields.

Aerobic radical-cascade cycloaddition of isocyanides, selenium and imidamides: facile access to 1,2,4-selenadiazoles under metal-free conditions

Co-reporter:Yi Fang;Zheng-Lin Zhu;Pei Xu;Shun-Yi Wang

Green Chemistry (1999-Present) 2017 vol. 19(Issue 7) pp:1613-1618

Publication Date(Web):2017/04/03

DOI:10.1039/C6GC03521C

A novel and facile metal-free method for the green synthesis of 1,2,4-selenadiazol-5-amine derivatives through the aerobic radical-cascade multi-component reactions of isocyanides, selenium powder and imidamides is reported herein. O2 in the air was employed as the green oxidant to achieve the cycloaddition with the generation of H2O as the sole by-product. It also features good functional group compatibility and broad substrate scope. In addition, this method was successfully applied to the functionalization of biologically active molecules.

Synthesis of fused indoline heterocycles via dearomatization of indoles with α-bromohydrazones: a systematic study on the substrates

Co-reporter:Wen-Bin Cao;Xiao-Ping Xu

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 7) pp:1651-1654

Publication Date(Web):2017/02/15

DOI:10.1039/C6OB02362B

An efficient metal-free dearomatization of indoles with α-bromohydrazones is reported. Various fused indoline heterocycles, which are potentially biologically active, were achieved in good yields (up to 94%) under mild conditions. A systematic study on electronic- and steric effects of substrate and reagents revealed that they have great influence upon the reaction. Based on this, the scope of indoles and α-bromohydrazones was widely exploited.

Silver-catalyzed tandem nucleophilic addition/cycloisomerization of ortho-alkynylbenzaldehydes: Regioselective synthesis of functionalized 1H-isochromene derivatives

Co-reporter:Fang-Hui Li, Jian Li, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2017 Volume 73, Issue 39(Issue 39) pp:

Publication Date(Web):28 September 2017

DOI:10.1016/j.tet.2017.07.051

An efficient silver-catalyzed domino cycloisomerization reaction for regioselective assembly of 1H-isochromene derivatives from o-alkynylaryl aldehydes with enaminones as the external nuclephiles is developed. This protocol affords isochromene derivatives in moderate to good yields under simple and mild reaction conditions.Download high-res image (100KB)Download full-size image

Novel oxazole-based emitters for high efficiency fluorescent OLEDs: Synthesis, characterization, and optoelectronic properties

Co-reporter:Zhen-Hua Xing, Jin-Yong Zhuang, Xiao-Ping Xu, Shun-Jun Ji, Wen-Ming Su, Zheng Cui

Tetrahedron 2017 Volume 73, Issue 15(Issue 15) pp:

Publication Date(Web):13 April 2017

DOI:10.1016/j.tet.2017.02.049

Two novel oxazole derivatives 4-(6-(4,5-diphenyloxazol-2-yl)pyridin-3-yl)-N,N-diphenylaniline (TPA-PPO) and 2-(5-(4-(9H-carbazol-9-yl)phenyl)pyridin-2-yl)-4,5-diphenyloxazole (CzPh-PPO) have been designed and synthesized. The photophysical, electrochemical and thermal characters of the compounds were systematically investigated, which consistent well with the theoretical DFT calculations. TPA-PPO and CzPh-PPO exhibit high photoluminescent quantum yield of 0.63 and 0.59, respectively. The device using TPA-PPO as the dopant showed deep blue emission with a high EQE of 1.77%. A white OLED was obtained using the single emitter of CzPh-PPO with an EQE of 1.24%.Download high-res image (145KB)Download full-size image

The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions

Co-reporter:Zheng-Yang Gu, Jia-Jia Cao, Shun-Yi Wang and Shun-Jun Ji

Chemical Science 2016 vol. 7(Issue 7) pp:4067-4072

Publication Date(Web):11 Mar 2016

DOI:10.1039/C6SC00240D

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiazine derivatives via formation of two C–S bonds under transition metal-free, additive-free and oxidant-free conditions. K2S not only provides the sulfur insertion source, but also ignites the reaction through the formation of a trisulfur radical anion and electrons in DMF.

Palladium-Catalyzed Cyclization of Alkenes with Organohalides

Co-reporter:Xue-Qiang Chu, Dan Liu, Zhen-Hua Xing, Xiao-Ping Xu, and Shun-Jun Ji

Organic Letters 2016 Volume 18(Issue 4) pp:776-779

Publication Date(Web):February 2, 2016

DOI:10.1021/acs.orglett.6b00035

A palladium-catalyzed tandem C–Br/C–H functionalization and cyclization of alkenes with organohalides is reported. This reaction provides an operationally simple method for the synthesis of various fluorene, pyrroloindole, and benzoxazine derivatives, which are useful pharmaceutical framework and photoelectronic devices. Two new C–C/O bonds, a quaternary carbon center and a new ring, are simultaneously formed in this one-pot reaction.

Palladium-Catalyzed Cascade Arene/Alkyne Annulation: Synthesis of Fluorene-Benzoxazine Derivatives

Co-reporter:Zhong-Jian Cai, Fang-Hui Li, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2016 Volume 18(Issue 19) pp:4810-4813

Publication Date(Web):September 12, 2016

DOI:10.1021/acs.orglett.6b02224

A palladium-catalyzed cascade arene/alkyne annulation reaction for the synthesis of fluorene-benzoxazine derivatives is developed. This transformation involves a 6-exo-dig cyclization, a 1,3-oxazine vinylpalladium intermediate, and a C–H bond activation.

Pd-Catalyzed Intramolecular Heck Reaction, C(sp2)–H Activation, 1,4-Pd Migration, and Aminopalladation: Chemoselective Synthesis of Dihydroindeno[1,2,3-kl]acridines and 3-Arylindoles

Co-reporter:Zheng-Yang Gu, Cheng-Guo Liu, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2016 Volume 18(Issue 10) pp:2379-2382

Publication Date(Web):May 3, 2016

DOI:10.1021/acs.orglett.6b00843

Palladium-catalyzed intramolecular Heck reaction and aminopalladation of N-(2-(1-phenylvinyl)phenyl)aniline for the efficient synthesis of dihydroindeno[1,2,3-kl]acridines and 3-arylindoles via tuning of the phosphine ligands and solvents under two optimized conditions are reported. The reaction follows a 1,4-Pd migration, aminopalladation, C(sp2)–H activation, as well as five- and six-membered-ring fusion to form different products. The dihydroindeno[1,2,3-kl]acridine derivatives showed higher triplet energy (ET) levels than common blue phosphorescent dopant and may serve as good host candidates for blue triplet emitters.

Sulfuration of the C(sp2)–H bond of enaminones: a protocol for the synthesis of thioether using elemental sulfur as a sulfurating reagent

Co-reporter:Li-Fang Yang, Cheng-Guo Liu, Xiao-Ping Xu and Shun-Jun Ji

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 10) pp:2993-2999

Publication Date(Web):04 Feb 2016

DOI:10.1039/C5OB02619A

Sulfuration reaction of the C(sp2)–H bond of enaminones with elemental sulfur in the presence of CuBr/K3PO4 was carried out. It provided an efficient method for the synthesis of thioethers in moderate to good yields. The protocol was also applicable to synthesize selenides when selenium powder was used instead of sulfur powder.

Co(acac)2/O2-catalyzed oxidative isocyanide insertion with 2-vinylanilines: efficient synthesis of 2-aminoquinolines

Co-reporter:Pei Xu, Tong-Hao Zhu, Tian-Qi Wei, Shun-Yi Wang and Shun-Jun Ji

RSC Advances 2016 vol. 6(Issue 39) pp:32467-32470

Publication Date(Web):11 Mar 2016

DOI:10.1039/C6RA03216H

A series of 2-aminoquinolines were afforded by Co(acac)2 catalyzed isocyanide insertion with 2-vinylanilines under an O2 atmosphere. This reaction not only uses low toxicity Co(acac)2 as the catalyst and oxygen as the oxidant, but also allows the construction of new C(sp2)–C(sp2) and C(sp2)–N bonds in a single-step.

Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

Co-reporter:Hui-Wen Bai, Zhong-Jian Cai, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2015 Volume 17(Issue 12) pp:2898-2901

Publication Date(Web):June 4, 2015

DOI:10.1021/acs.orglett.5b01000

A novel synthetic approach toward 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles by aerobic oxidative cycloaddition of α-chlorotosylhydrazone with primary aryl amine has been developed. Significantly, the reaction proceeds smoothly to afford 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles under catalyst-free, metal-free, azide-free, and peroxide-free conditions.

Synthesis of Carbodiimides by I2/CHP-Mediated Cross-Coupling Reaction of Isocyanides with Amines under Metal-Free Conditions

Co-reporter:Tong-Hao Zhu, Shun-Yi Wang, Yang-Qing Tao, and Shun-Jun Ji

Organic Letters 2015 Volume 17(Issue 8) pp:1974-1977

Publication Date(Web):March 31, 2015

DOI:10.1021/acs.orglett.5b00722

An I2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via C–N formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides an efficient approach for symmetric and unsymmetric functionalized carbodiimide derivative synthesis under mild conditions.

Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines

Co-reporter:Zhong-Jian Cai, Chao Yang, Shun-Yi Wang and Shun-Jun Ji

Chemical Communications 2015 vol. 51(Issue 75) pp:14267-14270

Publication Date(Web):12 Aug 2015

DOI:10.1039/C5CC06510K

A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed. This tandem cross-coupling protocol represents a simple, efficient, step- and atom-economic approach for the construction of scarcely known polyene-substituted benzo[d][1,3]oxazines in moderate to excellent yields with a broad substrate scope.

Cobalt-Catalyzed Intermolecular Oxidative Isocyanide Insertion with Two Amines: An Approach to Guanidines

Co-reporter:Tong-Hao Zhu;Shun-Yi Wang;Tian-Qi Wei

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 4) pp:823-828

Publication Date(Web):

DOI:10.1002/adsc.201400911

Synthesis and characterization on novel fluorescent sensors for Pd2+/Pd0 with high selectivity

Co-reporter:You Zi, Hua Meng, Xue-Qiang Chu, Xiao-Ping Xu and Shun-Jun Ji

RSC Advances 2015 vol. 5(Issue 33) pp:26092-26096

Publication Date(Web):06 Mar 2015

DOI:10.1039/C5RA01343G

Novel fluorescent sensors L1–L3 based on triaryl 1H-imidazo[4,5-b]pyrazine have been synthesized through a new and simple route from inexpensive and readily available materials in one pot. They exhibited high selectivity for palladium detection (oxidation states of 0 and +2) based on the fluorescence quenching effect.

Synthesis of 7-hydroxy-6,7-dihydro-indole and 6′,7′-dihydro-3,7′-biindole derivatives from domino reactions of arylglyoxals or methyl ketones with enamines

Co-reporter:Xin-Mou Lu, Zhong-Jian Cai, Jian Li, Shun-Yi Wang and Shun-Jun Ji

RSC Advances 2015 vol. 5(Issue 64) pp:51501-51507

Publication Date(Web):04 Jun 2015

DOI:10.1039/C5RA09478J

A series of interesting 7-hydroxy-2-aryl-6,7-dihydro-indol-4(5H)-ones 3 was successfully synthesized in moderate to good yields by the domino reactions of different arylglyoxals 1 with enamines 2 under catalyst-free conditions. 7-Hydroxy-2-aryl-6,7-dihydro-indol-4(5H)-ones 3 could also be prepared in moderate yields by the iodine-promoted one pot-two step reactions of methyl ketones 6 with enamines 2. The reaction of 3a with N-methyl indole 7a in the presence of PTSA afforded 2′-aryl-6′,7′-dihydro-[3,7′-biindol]-4′(5′H)-ones 8a in 81% yield. In addition, 3,7′-bis-indoles 8 could also be observed in 47–73% yields by one pot domino reaction of arylglyoxals 1 with enamines 2 and indoles 7 over two steps. This protocol provides a simple and practical method to construct diverse 7-hydroxy-6,7-dihydro-indole derivatives 3 and 3,7′-bis-indoles 8 from easily obtained starting materials.

Synthesis of functionalized benzoxazines by copper-catalyzed C(sp3)–H bond functionalization of acetonitrile with olefinic amides

Co-reporter:Xue-Qiang Chu, Xiao-Ping Xu, Hua Meng and Shun-Jun Ji

RSC Advances 2015 vol. 5(Issue 83) pp:67829-67832

Publication Date(Web):03 Aug 2015

DOI:10.1039/C5RA14729H

A copper-mediated oxycyanomethylation reaction of olefinic amides with acetonitrile was developed for the synthesis of important benzoxazine derivatives. The reactions involve the activation of the C(sp3)–H bond of acetonitrile and radical cyclization processes for the construction of new C–C and C–O bonds.

Syntheses and structural characterization of σ-/π-aryloxo cobalt(II) complexes and radical aryloxo sodium complex

Co-reporter:Chun-Xiang Yuan, Kai-Da Zhou, Xiao-Ping Xu, Yong Zhang, Shun-Jun Ji

Polyhedron 2015 87() pp: 245-250

Publication Date(Web):

DOI:10.1016/j.poly.2014.11.032

Palladium-Catalyzed Regioselective C–H Acylation of Biaryl-2-amines

Co-reporter:Zhong-Jian Cai, Chao Yang, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry 2015 Volume 80(Issue 16) pp:7928-7936

Publication Date(Web):July 20, 2015

DOI:10.1021/acs.joc.5b00962

A palladium-catalyzed efficient C–H acylation reaction of biaryl-2-amines and aromatic aldehydes is developed. This dehydrogenative cross-coupling protocol could furnish monoacylation and diacylation products in moderate to good yields with a broad substrate scope and good regioselectivity.

Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives

Co-reporter:Ying Zhang, Jing-Lei Chen, Zhen-Bang Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:10643-10650

Publication Date(Web):October 9, 2015

DOI:10.1021/acs.joc.5b01758

An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.

Metal-free one-pot domino reaction: chemoselective synthesis of polyarylated oxazoles

Co-reporter:Hua Meng, You Zi, Xiao-Ping Xu, Shun-Jun Ji

Tetrahedron 2015 Volume 71(Issue 23) pp:3819-3826

Publication Date(Web):10 June 2015

DOI:10.1016/j.tet.2015.03.119

A convenient method has been established for the chemoselective synthesis of polyarylated oxazoles from aromatic aldehydes and 2-cyano heteroarenes. The protocol presents a novel one-pot methodology for the synthesis of oxazole derivatives without any metal catalysts or extra oxidants. Photophysical test showed that the polyarylated oxazoles may serve as potential fluorescent materials with blue light-emitting properties.

Acyclic aminocarbene-like palladium complex-catalyzed Suzuki–Miyaura reaction at low catalyst loadings

Co-reporter:Yi Fang, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2015 Volume 71(Issue 52) pp:9679-9683

Publication Date(Web):30 December 2015

DOI:10.1016/j.tet.2015.10.033

A series of air-stable aminocarbene-like palladium(II) complexes were easily prepared by the reaction of bis-aromaticisocyanide-dichloropalladium(II) with N-arylbenzamidines. 0.1 mol % of the optimal palladium complex 3a showed excellent catalytic activity for Suzuki–Miyaura cross-coupling reaction at room temperature and the desired products were isolated in up to 98% yields. Moreover, a large-scale reaction showed that 0.01 mol % 3a was enough to catalyze the coupling reaction efficiently at room temperature to give the desired product in 93% yield.

Synthesis of phthalimides through 1,3-dipolar cycloaddition of CO2 with isocyanides and arynes

Co-reporter:Yi Fang, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2015 Volume 71(Issue 18) pp:2768-2771

Publication Date(Web):6 May 2015

DOI:10.1016/j.tet.2015.02.051

A new practical synthesis of phthalimides through 1,3-dipolar cycloaddition of CO2 with isocyanides and in situ generated aryne is reported here. A series of phthalimide derivatives are observed in moderate to good yields under mild conditions.

Copper-catalyzed aerobic oxidative dicarbonylation of indoles utilizing α-carbonyl aldehydes

Co-reporter:Jin-Ming Yang, Zhong-Jian Cai, Qing-Dong Wang, Dong Fang, Shun-Jun Ji

Tetrahedron 2015 Volume 71(Issue 38) pp:7010-7015

Publication Date(Web):23 September 2015

DOI:10.1016/j.tet.2015.07.004

An efficient and practical protocol for copper-catalyzed aerobic oxidative dicarbonylation of indoles using α-carbonyl aldehydes to construct C-3 indole-substituted 1,2-diketones is developed. Various C-3 indole-substituted 1,2-diketones were observed in good to excellent yields under mild reaction conditions. This transformation used air as an ideal oxidant and produced water as the only by-product.

Palladium-Catalyzed Cascade Reactions of Isocyanides with Enaminones: Synthesis of 4-Aminoquinoline Derivatives

Co-reporter:Zheng-Yang Gu, Tong-Hao Zhu, Jia-Jia Cao, Xiao-Ping Xu, Shun-Yi Wang, and Shun-Jun Ji

ACS Catalysis 2014 Volume 4(Issue 1) pp:49

Publication Date(Web):December 2, 2013

DOI:10.1021/cs400904t

A method for palladium-catalyzed cascade reactions of isocyanides with enaminones has been developed. This methodology provides a direct approach to 4-aminoquinoline derivatives under mild conditions with up to 98% yields.Keywords: amino quinoline; cascade reaction; isocyanide; palladium

Synthesis of Isatins by I2/TBHP Mediated Oxidation of Indoles

Co-reporter:You Zi, Zhong-Jian Cai, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2014 Volume 16(Issue 11) pp:3094-3097

Publication Date(Web):May 21, 2014

DOI:10.1021/ol501203q

An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.

I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

Co-reporter:Zhong-Jian Cai, Xin-Mou Lu, You Zi, Chao Yang, Ling-Jie Shen, Jian Li, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2014 Volume 16(Issue 19) pp:5108-5111

Publication Date(Web):September 24, 2014

DOI:10.1021/ol502431b

An efficient I2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C–N/N–N bond formation and S–N cleavage has been developed. This protocol represents a simple, general, and efficient approach for the construction of 1,2,3-triazoles under metal-free and azide-free conditions by utilizing a catalytic amount of I2.

Metal-free oxidative direct C(sp3)–H bond functionalization of ethers with α,α-diaryl allylic alcohols

Co-reporter:Xue-Qiang Chu, Hua Meng, You Zi, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2014 vol. 50(Issue 68) pp:9718-9721

Publication Date(Web):27 Jun 2014

DOI:10.1039/C4CC04282D

A metal-free method for direct C(sp3)–H bond functionalization of simple ethers with α,α-diaryl allylic alcohols is described. The established protocol provides facile access to α-aryl-β-oxyalkylated carbonyl ketones via radical addition and a 1,2-aryl migration cascade process. An application of the product has been demonstrated in the synthesis of a serotonin antagonist.

Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration

Co-reporter:Xue-Qiang Chu, You Zi, Hua Meng, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2014 vol. 50(Issue 57) pp:7642-7645

Publication Date(Web):22 May 2014

DOI:10.1039/C4CC02114B

A novel radical phosphinylation of α,α-diaryl allylic alcohols with arylphosphine oxides was described for the direct preparation of α-aryl-β-phosphinylated carbonyl ketones in medium to good yields via 1,2-aryl migration. In this reaction, formation of new C(Ar)–C(sp3) and C(sp3)–P bonds was observed.

Mn(III)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated phenanthridines

Co-reporter:Jia-Jia Cao, Xiang Wang, Shun-Yi Wang and Shun-Jun Ji

Chemical Communications 2014 vol. 50(Issue 85) pp:12892-12895

Publication Date(Web):01 Sep 2014

DOI:10.1039/C4CC05324A

Mn(III)-mediated reactions of 2-isocyanobiaryls with 1,3-dicarbonyl compounds were described for the construction of 6-alkylated and 6-monofluoro-alkylated phenanthridines in moderate to good yields. The reaction involves formation of two new C–C bonds and one C–C bond cleavage.

Palladium-Catalyzed Formylation of Aryl Halides with tert-Butyl Isocyanide

Co-reporter:Xiao Jiang, Jin-Mei Wang, Ying Zhang, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

Organic Letters 2014 Volume 16(Issue 13) pp:3492-3495

Publication Date(Web):June 23, 2014

DOI:10.1021/ol5014262

A novel palladium-catalyzed formylation of aryl halides with isocyanide in the presence of Et3SiH has been demonstrated, which provides a strategy toward important aldehydes with moderate to excellent yield. The advantage of this reaction includes milder conditions, convenient operation, lower toxicity, and wide functional group tolerance.

Co(acac)2/O2-Mediated Oxidative Isocyanide Insertion with 2-Aryl Anilines: Efficient Synthesis of 6-Amino Phenanthridine Derivatives

Co-reporter:Tong-Hao Zhu, Shun-Yi Wang, Yang-Qing Tao, Tian-Qi Wei, and Shun-Jun Ji

Organic Letters 2014 Volume 16(Issue 4) pp:1260-1263

Publication Date(Web):February 7, 2014

DOI:10.1021/ol500286x

A novel and efficient protocol for the creation of 6-amino phenanthridine derivatives by Co(acac)2-catalyzed isocyanide insertion with 2-aryl anilines under an O2 atmosphere via homolytic aromatic substitution (HAS) type C–H functionalization has been developed. This reaction not only proceeds smoothly utilizing O2 as the oxidant but also provides a new approach to construct phenanthridine derivatives utilizing readily available 2-aryl anilines with isocyanides instead of 2-isocyanobiaryls with different radical precursors.

tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)–H/C(sp2)–H bond functionalization

Co-reporter:Jia-Jia Cao, Tong-Hao Zhu, Shun-Yi Wang, Zheng-Yang Gu, Xiang Wang and Shun-Jun Ji

Chemical Communications 2014 vol. 50(Issue 49) pp:6439-6442

Publication Date(Web):24 Feb 2014

DOI:10.1039/C4CC00743C

An efficient method for the construction of 6-alkyl phenanthridines by tert-butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane was established. Two new C–C bonds were formed in this reaction via a sequential C(sp3)–H/C(sp2)–H bond functionalization under metal-free conditions.

Spiro-annulated hole-transport material outperforms NPB with higher mobility and stability in organic light-emitting diodes

Co-reporter:Hua Chen, Chun-Hong Gao, Zuo-Quan Jiang, Lei Zhang, Lin-Song Cui, Shun-Jun Ji, Liang-Sheng Liao

Dyes and Pigments 2014 Volume 107() pp:15-20

Publication Date(Web):August 2014

DOI:10.1016/j.dyepig.2014.03.006

•A more stable host materials STNPB is constructed using spirostrue.•A phosphorescent device is used to evaluate the performance.•A 1.5 times enhancement in lifetime is obtained.•Polarized optical microscopy is used to reveal the process of film heating.A novel multifunctional spiro-annulated fluorene/triarylamine based compound (STNPB) has been designed, synthesized and characterized. It exhibits a high glass transition temperature of 140 °C, due to the rigid spiro-configuration molecular structure. According to its suitable energy level and triplet energy (2.34 eV), improved performances, such as lower driving voltage, enhanced device power efficiency, and longer stability, are shown in organic light-emitting diodes with STNPB as the hole-transport material, compared with the ones with the widely used arylamine derivative N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine (NPB). Through further studies, it has been demonstrated that the enhanced stability is attributed to suppressed crystallization process as a result of employing STNPB instead of NPB as the hole-transport material.

Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

Co-reporter:Rong Wang, Shun-Yi Wang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 11) pp:1735-1740

Publication Date(Web):15 Jan 2014

DOI:10.1039/C3OB42570C

A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C–C bond cleavage in the presence of water under mild conditions.

Synthesis of 1,4-dihydroquinoline derivatives under transition-metal-free conditions and their diverse applications

Co-reporter:Xue-Qiang Chu, You Zi, Hua Meng, Xiao-Ping Xu and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 24) pp:4243-4251

Publication Date(Web):22 Apr 2014

DOI:10.1039/C4OB00475B

A transition-metal-free process for the synthesis of 1,4-dihydroquinoline derivatives starting from simple enaminones with aldehydes via intermolecular cascade cyclization in a one-pot protocol is developed. This methodology affords a variety of products in moderate to good yields. Particularly, the use of the enaminone fragment in 1,4-dihydroquinoline derivatives 3 as a leaving group for further diverse applications with C-nucleophiles is proved to be feasible.

One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

Co-reporter:Xin-Mou Lu, Jian Li, Zhong-Jian Cai, Rong Wang, Shun-Yi Wang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 46) pp:9471-9477

Publication Date(Web):01 Oct 2014

DOI:10.1039/C4OB01580K

An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen reaction and cyclization under basic conditions has been reported. The desired products could be obtained in moderate to good yields.

In(OTf)3-catalyzed chemoselective alkylation of tryptamines with 2-oxo-1-pyrrolidine derivatives

Co-reporter:You Zi, Xue-Qiang Chu, Xin-Mou Lu, Shun-Yi Wang and Shun-Jun Ji

RSC Advances 2014 vol. 4(Issue 9) pp:4609-4618

Publication Date(Web):18 Oct 2013

DOI:10.1039/C3RA44196B

The chemoselective alkylation of tryptamine derivatives with 2-oxo-1-pyrrolidine compounds, catalyzed by In(OTf)3, was investigated. A series of 2-alkyl and N-alkyl tryptamine derivatives were synthesized under mild conditions with good total yields (up to 99%) and chemoselectivity (up to 95:5).

Facile Synthesis of 4-H-Pyran Derivatives Bearing Indole Skeleton via [3+3] Cyclization of 3-Indolyl-3-oxopropanenitriles with Dialkyl Acetylenedicarboxylates and Isocyanides

Co-reporter:Ping Song;Lili Zhao;Shunjun Ji

Chinese Journal of Chemistry 2014 Volume 32( Issue 5) pp:381-386

Publication Date(Web):

DOI:10.1002/cjoc.201400155

Abstract

An efficient multicomponent reaction of 3-indolyl-3-oxopropanenitriles with dialkyl acetylenedicarboxylates and isocyanides under mild conditions leading to highly functionalized 6-(indol-3-yl)-4H-pyrans in moderate to good yields has been developed.

Metal-Free Oxidative Radical Addition of Carbonyl Compounds to ,-Diaryl Allylic Alcohols: Synthesis of Highly Functionalized Ketones

Co-reporter:Xue-Qiang Chu;Hua Meng;You Zi;Dr. Xiao-Ping Xu;Dr. Shun-Jun Ji

Chemistry - A European Journal 2014 Volume 20( Issue 51) pp:17198-17206

Publication Date(Web):

DOI:10.1002/chem.201404463

Abstract

A metal-free direct alkylation of simple carbonyl compounds (ketones, esters, and amides) with α,α-diaryl allylic alcohols is described. The protocol provides facile access to highly functionalized dicarbonyl ketones by a radical addition/1,2-aryl migration cascade. The regioselectivity of the reaction was precisely controlled by the nature of the carbonyl compound.

Chemoselective Synthesis of Polycyclic Spiroindolines and Polysubstituted Pyrroles via the Domino Reaction of 2-Isocyanoethylindoles

Co-reporter:Xiang Wang, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry 2014 Volume 79(Issue 18) pp:8577-8583

Publication Date(Web):August 22, 2014

DOI:10.1021/jo501143m

Chemoselective 2-isocyanoethylindole-based domino reactions for the construction of polycyclic spiroindoline derivatives and polysubstituted pyrroles have been developed. The reaction of 2-isocyanoethylindoles and gem-diactivated olefins lead to the polycyclic spiroindoline derivatives (up to 92% yields) in EtOH under reflux conditions. Furthermore, the three-component reaction of 2-isocyanoethylindoles with gem-diactivated olefins and secondary amines afford polysubstituted pyrroles (in moderate yields) in CH3CN under reflux conditions.

Palladium-Catalyzed One-Pot Synthesis of Quinazolinones via tert-Butyl Isocyanide Insertion

Co-reporter:Xiao Jiang, Ting Tang, Jin-Mei Wang, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2014 Volume 79(Issue 11) pp:5082-5087

Publication Date(Web):May 8, 2014

DOI:10.1021/jo500636y

A novel palladium-catalyzed three-component reaction for the synthesis of quinazolin-4(3H)-ones from readily available 2-aminobenzamides and aryl halides via a palladium-catalyzed isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs quinazolin-4(3H)-ones in moderate to excellent yields with the advantages of operational simplicity.

A highly diastereoselective synthesis of chroman derivatives bearing spirocyclic N,O-acetals skeleton via a one-pot tandem reaction

Co-reporter:Yu Zhou, Kai-Da Zhou, Xiao-Ping Xu, Ya-Nan Zhu, Zhen Wu, Shun-Jun Ji

Tetrahedron 2014 70(51) pp: 9644-9651

Publication Date(Web):

DOI:10.1016/j.tet.2014.10.073

Silver-catalyzed 2-isocyanobiaryls insertion/cyclization with phosphine oxides: synthesis of 6-phosphorylated phenanthridines

Co-reporter:Jia-Jia Cao, Tong-Hao Zhu, Zheng-Yang Gu, Wen-Juan Hao, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2014 70(39) pp: 6985-6990

Publication Date(Web):

DOI:10.1016/j.tet.2014.07.078

NiCl2-catalyzed cascade reaction of isocyanides with functionalized anilines

Co-reporter:Gao-Nan Wang, Tong-Hao Zhu, Shun-Yi Wang, Tian-Qi Wei, Shun-Jun Ji

Tetrahedron 2014 70(43) pp: 8079-8083

Publication Date(Web):

DOI:10.1016/j.tet.2014.08.032

Iodine-Catalyzed Cascade Formal [3 + 3] Cycloaddition Reaction of Indolyl Alcohol Derivatives with Enaminones: Constructions of Functionalized Spirodihydrocarbolines

Co-reporter:Wen-Juan Hao, Shun-Yi Wang, and Shun-Jun Ji

ACS Catalysis 2013 Volume 3(Issue 11) pp:2501

Publication Date(Web):October 3, 2013

DOI:10.1021/cs400703u

A simple and practical method for the synthesis of spirodihydrocarboline derivatives from indolyl alcohol derivatives with enaminones via an iodine-catalyzed cascade formal [3 + 3] cycloaddition reaction has been developed. The reaction afforded the desired products under mild conditions in moderate to good yields with excellent regioselectivities.Keywords: carbolines; cascade reaction; formal [3 + 3] cycloaddition reaction; indolyl alcohol; iodine

Dual 1,3-dipolar cycloaddition of carbon dioxide: two CO bonds of CO2 react in one reaction

Co-reporter:Li-Li Zhao, Shun-Yi Wang, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2013 vol. 49(Issue 25) pp:2569-2571

Publication Date(Web):17 Jan 2013

DOI:10.1039/C3CC38526D

The first investigation into two CO bonds of CO2 reacting in one reaction through dual 1,3-dipolar cycloaddition of CO2 with isocyanides and dialkyl acetylenedicarboxylates has been reported. The reaction proceeded efficiently at 80 °C at a pressure of 1 atm of CO2, affording symmetric 1,6-dioxospiro[4,4]nonane-3,8-diene derivatives in moderate yields.

I2/TBHP-Catalyzed Chemoselective Amination of Indoles

Co-reporter:Zhong-Jian Cai, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2013 Volume 15(Issue 20) pp:5226-5229

Publication Date(Web):September 12, 2013

DOI:10.1021/ol4023936

A novel I2/TBHP-mediated direct oxidative diamination reaction of indoles with anilines was developed. The reaction proceeded smoothly under aqueous and open air reaction conditions. This protocol provides a practical synthetic method for the synthesis of Tryptanthrin and the construction of N–C3 linked pyrrolidinoindolines which is the core structure of Psychotrimine.

Highly Efficient Chemoselective Synthesis of Polysubstituted Pyrroles via Isocyanide-Based Multicomponent Domino Reaction

Co-reporter:Xiang Wang, Xiao-Ping Xu, Shun-Yi Wang, Weiqun Zhou, and Shun-Jun Ji

Organic Letters 2013 Volume 15(Issue 16) pp:4246-4249

Publication Date(Web):August 7, 2013

DOI:10.1021/ol401976w

A multicomponent domino reaction for the chemoselective, catalyst-free synthesis of polysubstituted pyrroles from readily available isocyanides, primary or secondary amines, and gem-diactivated olefins has been developed. Structurally diverse pyrroles were obtained in moderate to good yields under mild conditions.

Isocyanide-Based Multicomponent Reactions: Catalyst-Free Stereoselective Construction of Polycyclic Spiroindolines

Co-reporter:Xiang Wang, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2013 Volume 15(Issue 8) pp:1954-1957

Publication Date(Web):April 8, 2013

DOI:10.1021/ol400606c

A novel catalyst-free one-pot tandem reaction for the stereoselective construction of polycyclic spiroindolines was developed. This method offers a straightforward access to structurally diverse polycyclic spiroindoline derivatives in high yields (up to 90%) with excellent levels of diastereoselectivity.

Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines

Co-reporter:Zhong-Jian Cai;Shun-Yi Wang

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 13) pp:2686-2692

Publication Date(Web):

DOI:10.1002/adsc.201300333

Asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media

Co-reporter:Ying Zhang, Shun-Yi Wang, Xiao-Ping Xu, Ran Jiang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 12) pp:1933-1937

Publication Date(Web):01 Feb 2013

DOI:10.1039/C3OB00045A

Organocatalyzed asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media has been developed. The reactions proceeded efficiently in the presence of the MacMillan catalyst to give the desired products in good to excellent yields with moderate diastereoselectivities and excellent enantioselectivities.

In(OTf)3 catalyzed C3-benzylation of indoles with benzyl alcohols in water

Co-reporter:Lin Wu, Ran Jiang, Jin-Ming Yang, Shun-Yi Wang and Shun-Jun Ji

RSC Advances 2013 vol. 3(Issue 16) pp:5459-5464

Publication Date(Web):08 Feb 2013

DOI:10.1039/C3RA40251G

A novel C3-benzylation of indoles through C–O bond activation of benzyl alcohols catalyzed by In(OTf)3 in water has been developed. The reactions proceed smoothly in presence of In(OTf)3 as the catalyst without the use of any bases, ligands or other additives to perform the desired product in moderate to excellent yields.

Catalyst-free diastereoselective synthesis of 2-methyl-4-amino-1,2,3,4-tetrahydro-quinoline derivatives in water

Co-reporter:Lin Wu, Ran Jiang, Jin-Ming Yang, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron Letters 2013 Volume 54(Issue 22) pp:2849-2852

Publication Date(Web):29 May 2013

DOI:10.1016/j.tetlet.2013.03.091

A diastereoselective synthesis of 2-methyl-4-amino-1,2,3,4-tetrahydro-quinoline derivatives was achieved through the reaction of aromatic amines and tert-enamides in water under reflux conditions. The desired products could be obtained in moderate to excellent yields utilizing water as solvent without any catalyst or additive.

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides via tert-Butyl Isocyanide Insertion

Co-reporter:Ting Tang, Xiang-Dong Fei, Zhi-Yuan Ge, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2013 Volume 78(Issue 7) pp:3170-3175

Publication Date(Web):February 25, 2013

DOI:10.1021/jo4001096

A simple and efficient palladium-catalyzed carbonylative Sonogashira coupling via tert-butyl isocyanide insertion has been developed, which demonstrates the utility of isocyanides in intermolecular C–C bond construction. This methodology provides a novel pathway for the synthesis of alkynyl imines which can undergo simple silica gel catalyzed hydrolysis to afford alkynones. The approach is tolerant of a wide range of substrates and applicable to library synthesis.

I2/O2-Promoted Domino Reactions of Isatins or 3-Hydroxyindolin-2-one Derivatives with Enaminones

Co-reporter:Wen-Juan Hao, Jian-Qiang Wang, Xiao-Ping Xu, Shi-Lei Zhang, Shun-Yi Wang, and Shun-Jun Ji

The Journal of Organic Chemistry 2013 Volume 78(Issue 24) pp:12362-12373

Publication Date(Web):December 2, 2013

DOI:10.1021/jo401773j

I2-promoted domino reactions of isatins or 3-hydroxyindolin-2-one derivatives with enaminones under O2 conditions have been established. The reactions of isatins with enaminones afforded functionalized tetracyclic pyrrolo[2,3,4-kl]acridine derivatives in moderate to good yields through domino cyclization and C–H oxidation. The reactions of 3-hydroxyindolin-2-one derivatives with enaminones proceeded well to give functionalized pyrrolo[2,3,4-kl]acridine derivatives via tandem ring-opening/recyclization/methyl migration sequences with two C–C bonds cleaved.

3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C–C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives

Co-reporter:Rong Wang, Xiao-Ping Xu, Hua Meng, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2013 69(6) pp: 1761-1766

Publication Date(Web):

DOI:10.1016/j.tet.2012.11.088

TFA-catalyzed C–N bond activation of enamides with indoles: efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes

Co-reporter:Hai-Yan Xu, You Zi, Xiao-Ping Xu, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2013 69(5) pp: 1600-1605

Publication Date(Web):

DOI:10.1016/j.tet.2012.11.098

Cobalt-Catalyzed Oxidative Isocyanide Insertion to Amine-Based Bisnucleophiles: Diverse Synthesis of Substituted 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and 2-Aminobenzoxazoles

Co-reporter:Tong-Hao Zhu;Dr. Shun-Yi Wang;Gao-Nan Wang ;Dr. Shun-Jun Ji

Chemistry - A European Journal 2013 Volume 19( Issue 19) pp:5850-5853

Publication Date(Web):

DOI:10.1002/chem.201300239

Silicon-Based Material with Spiro-Annulated Fluorene/Triphenylamine as Host and Exciton-Blocking Layer for Blue Electrophosphorescent Devices

Co-reporter:Hua Chen;Dr. Zuo-Quan Jiang;Chun-Hong Gao;Mei-Feng Xu;Shou-Cheng Dong;Lin-Song Cui;Dr. Shun-Jun Ji;Dr. Liang-Sheng Liao

Chemistry - A European Journal 2013 Volume 19( Issue 35) pp:11791-11797

Publication Date(Web):

DOI:10.1002/chem.201301106

Abstract

A novel silicon-based compound, 10-phenyl-2′-(triphenylsilyl)-10H-spiro[acridine-9,9′-fluorene] (SSTF), with spiro structure has been designed, synthesized, and characterized. Its thermal, electronic absorption, and photoluminescence properties were studied. Its energy levels make it suitable as a host material or exciton-blocking material in blue phosphorescent organic light-emitting diodes (PhOLEDs). Accordingly, blue-emitting devices with iridium(III) bis[(4,6-difluorophenyl)-pyridinato-N,C²′]picolinate (FIrpic) as phosphorescent dopant have been fabricated and show high efficiency with low roll-off. In particular, 44.0 cd A⁻¹ (41.3 lm W⁻¹) at 100 cd m⁻² and 41.9 cd A⁻¹ (32.9 lm W⁻¹) at 1000 cd m⁻² were achieved when SSTF was used as host material; 28.1 lm W⁻¹ at 100 cd m⁻² and 20.6 lm W⁻¹ at 1000 cd m⁻² were achieved when SSTF was used as exciton-blocking layer. All of the results are superior to those of the reference devices and show the potential applicability and versatility of SSTF in blue PhOLEDs.

Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols

Co-reporter:Xue-Qiang Chu, Ran Jiang, Yi Fang, Zheng-Yang Gu, Hua Meng, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2013 69(3) pp: 1166-1174

Publication Date(Web):

DOI:10.1016/j.tet.2012.11.045

In(OTf)3 catalyzed N-benzylation of amines utilizing benzyl alcohols in water

Co-reporter:Jin-Ming Yang, Ran Jiang, Lin Wu, Xiao-Ping Xu, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2013 69(37) pp: 7988-7994

Publication Date(Web):

DOI:10.1016/j.tet.2013.07.010

Chemoselective synthesis of 3H-pyrrolo[2,3-c]quinolin-4(5H)-one derivatives from 3-phenacylideneoxindoles and substituted tosylmethyl isocyanide (TosMIC)

Co-reporter:Rong Wang, Shun-Yi Wang, Shun-Jun Ji

Tetrahedron 2013 69(51) pp: 10836-10841

Publication Date(Web):

DOI:10.1016/j.tet.2013.10.084

CuI/BF3·Et2O Cocatalyzed Aerobic Dehydrogenative Reactions of Ketones with Benzylamines: Facile Synthesis of Substituted Imidazoles

Co-reporter:Zhong-Jian Cai, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2012 Volume 14(Issue 23) pp:6068-6071

Publication Date(Web):November 20, 2012

DOI:10.1021/ol302955u

A novel CuI/BF3·Et2O/O2-mediated reaction utilizing ketones and benzylamines for the construction of substituted imidazoles in one step under mild conditions has been demonstrated. This protocol involved the removal of eight hydrogen atoms, the functionalization of four C(sp3)–H bonds and three new C–N bond formations.

Efficient Multicomponent Strategy to Pentacyclic Pyrazole-Fused Naphtho[1,8-fg]isoquinolines through Cleavage of Two Carbon–Carbon Bonds

Co-reporter:Wen-Juan Hao, Xiao-Ping Xu, Hui-Wen Bai, Shun-Yi Wang, and Shun-Jun Ji

Organic Letters 2012 Volume 14(Issue 18) pp:4894-4897

Publication Date(Web):September 12, 2012

DOI:10.1021/ol302452j

Multicomponent reactions of acenaphthylene-1,2-dione with diaroylmethanes and electron-rich pyrazol-5-amines have been discovered. A series of new and polyfunctionalized pentacyclic pyrazole-fused naphtho[1,8-fg]isoquinolines were regioselectively synthesized. The reactions were easy to perform simply by mixing three common reactants in AcOH. During these reaction processes, the insertion of active methylene of diaroylmethane into the sp2–sp2 C–C bond of the cyclohexa-2,5-dienone ring was readily achieved and two C–C bonds were cleaved under transition-metal-free conditions.

I-MCR-Ullmann cascade toward furo[2,3-b]indole scaffold

Co-reporter:Xu Zhu, Xiao-Ping Xu, Chang Sun, Tao Chen, Zhi-Liang Shen, Shun-Jun Ji

Tetrahedron 2011 67(34) pp: 6375-6381

Publication Date(Web):

DOI:10.1016/j.tet.2011.05.101

Conjugate Addition of Indoles to α,β-Unsaturated Ketones (Chalcones) Catalyzed by KHSO4 under Ultrasonic Conditions

Co-reporter:Xiao-Fei ZENG;Shu-Su SHEN

Chinese Journal of Chemistry 2007 Volume 25(Issue 12) pp:

Publication Date(Web):12 DEC 2007

DOI:10.1002/cjoc.200790328

Conjugate addition of indoles to a variety of α,β-unsaturated ketones (chalcones) mediated by a catalytic amount of KHSO₄ at room temperature under ultrasonic conditions to afford the corresponding Michael adducts in good to excellent yields was reported.

Synthesis of N-(α-Alkoxyalkyl)benzotriazoles Catalyzed by Acidic Ionic Liquid at Room Temperature

Co-reporter:Hong-Xia Wang;Da-Gong Gu

Chinese Journal of Chemistry 2007 Volume 25(Issue 7) pp:

Publication Date(Web):16 JUL 2007

DOI:10.1002/cjoc.200790167

N-(α-Alkoxyalkyl)benzotriazoles were synthesized via the condensation of benzotriazole with various aldehydes and alcohols catalyzed by acidic ionic liquid [hmim]HSO₄ at room temperature. The yield was up to 99%. This novel method was effective when triethoxymethane was utilized instead of alcohols. Moreover, acidic ionic liquid could be reused easily with no significant degradation of its catalytic activity.

Asymmetric Allyltributylstannane Addition to Ketones Catalyzed by Chiral Indium(III)-PYBOX Complex

Co-reporter:Jun Lu

Chinese Journal of Chemistry 2006 Volume 24(Issue 10) pp:

Publication Date(Web):2 OCT 2006

DOI:10.1002/cjoc.200690270

An indium complex of chiral pyridine bis(oxazoline) (PYBOX) has been applied to the catalytic asymmetric allylation of ketones. It has been found that this chiral indium complex is strong enough to promote the reaction of ketones with allyltributylstannane smoothly. The products were obtained in moderate yields with low to moderate enantioselectivities.

Enantioselective allylation of ketones catalyzed by chiral In(III)-PYBOX complexes

Co-reporter:Jun Lu, Mei-Ling Hong, Shun-Jun Ji, Yong-Chua Teo and Teck-Peng Loh

Chemical Communications 2005 (Issue 33) pp:4217-4218

Publication Date(Web):25 Jul 2005

DOI:10.1039/B507768K

In the presence of 20 mol% of chiral catalytic complex prepared from In(OTf)3 and chiral PYBOX, allyltributylstannane reacted with achiral ketones to afford the corresponding homoallylic alcohols in moderate to high enantioselectivities (54–95% ee), which constitutes the first example of enantioselective allylation of ketones catalyzed by the chiral In(III)-PYBOX complex.

Enantioselective allylation of aldehydes catalyzed by chiral indium(III) complexes immobilized in ionic liquids

Co-reporter:Jun Lu, Shun-Jun Ji and Teck-Peng Loh

Chemical Communications 2005 (Issue 18) pp:2345-2347

Publication Date(Web):15 Mar 2005

DOI:10.1039/B500086F

In the presence of chiral catalytic complexes prepared from In(OTf)3 and chiral PYBOX ligands, allytributylstannane reacted with aldehydes in ionic liquids to afford the corresponding homoallylic alcohols in high enantioselectivities (86–94% ee) and good yields (68–89%); the chiral catalysts immobilized in ionic liquids could be reused with comparable enantioselectivities and yields.

Ultrasound-promoted alkynylation of ethynylbenzene to ketones under solvent-free condition

Co-reporter:Shun-Jun Ji, Zhi-Liang Shen, Da-Gong Gu, Xiao-Ying Huang

Ultrasonics Sonochemistry 2005 Volume 12(Issue 3) pp:161-163

Publication Date(Web):February 2005

DOI:10.1016/j.ultsonch.2004.01.036

This paper described alkynylation of ethynylbenzene to ketones catalyzed by potassium tert-butoxide under solvent-free conditions in the presence of ultrasound irradiation.

An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation

Co-reporter:Shun-Jun Ji, Shun-Yi Wang

Ultrasonics Sonochemistry 2005 Volume 12(Issue 5) pp:339-343

Publication Date(Web):April 2005

DOI:10.1016/j.ultsonch.2004.05.003

PTSA catalyzes the Michael addition of indole to α,β-unsaturated carbonyl ketones under ultrasonic irradiation to afford the corresponding product β-indolylketones in excellent yields (up to 94%).

A Mild and Efficient Synthesis of 5-Oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran Derivatives in Room Temperature Ionic Liquids

Co-reporter:Jiang Zhao-Qin;Ji Shun-Jun;Lu Jun;Yang Jin-Ming

Chinese Journal of Chemistry 2005 Volume 23(Issue 8) pp:

Publication Date(Web):10 OCT 2005

DOI:10.1002/cjoc.200591085

A one-pot synthesis of a series of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives via three-component coupling reactions of aldehydes, dimedone and malononitrile in room temperature ionic liquids (RTILs) without any catalyst has been reported. In the meantime, the reuse of ionic liquids and the effect of different ionic liquids as solvent on the reaction have also been investigated.

Ultrasound-irradiated Michael addition of amines to ferrocenylenones under solvent-free and catalyst-free conditions at room temperature

Co-reporter:Jin-Ming Yang, Shun-Jun Ji, Da-Gong Gu, Zhi-Liang Shen, Shun-Yi Wang

Journal of Organometallic Chemistry 2005 Volume 690(Issue 12) pp:2989-2995

Publication Date(Web):15 June 2005

DOI:10.1016/j.jorganchem.2005.03.030

A facile Michael addition of ferrocenylenones with aliphatic amines under ultrasound irradiation in the absence of solvent and catalyst at room temperature can afford 1-ferrocenyl-3-amino carbonyl compounds rapidly in high yields, which is also efficient in the aza-Michael reaction of other α,β-unsaturated carbonyl compounds such as chalcone, carboxylic ester, etc. However, aromatic amines do not undergo the conjugate addition at all, and the reactions under existing methods do not proceed or take place in low yield after a long reaction time. Apart from experimental simplicity, generality and selectivity, the advantages of this methodology are the rapid, environmentally benign and less expensive processes, which will contribute to the progress of green chemistry.A facile Michael addition of ferrocenylenones with aliphatic amines under ultrasound irradiation in the absence of solvent and catalyst at room temperature can afford 1-ferrocenyl-3-amino carbonyl compounds rapidly in high yields, which is also efficient in the aza-Michael reaction of other α,β-unsaturated carbonyl compounds such as chalcone, carboxylic ester etc. Apart from experimental simplicity, generality and selectivity, the advantages of this methodology are the rapid, environmentally benign and less expensive processes, which will contribute to the progress of green chemistry.

Efficient FeIII-Catalyzed Synthesis of Bis(indolyl)methanes in Ionic Liquids

Co-reporter:Shun-Jun Ji;Min-Feng Zhou;Da-Gong Gu;Zhao-Qin Jiang;Teck-Peng Loh

European Journal of Organic Chemistry 2004 Volume 2004(Issue 7) pp:

Publication Date(Web):18 MAR 2004

DOI:10.1002/ejoc.200300719

An efficient synthesis of bis(indolyl)methanes through Fe^III-catalyzed electrophilic substitution reactions of indoles with various aldehydes in ionic liquid is described. It was found that the ionic liquids involving FeCl₃·6H₂O were the most efficient catalytic systems, and could be simply recycled without significant loss of activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

An efficient synthesis of ferrocenyl substituted 1,5-diketone and cyclic α,β-unsaturated ketones under ultrasound irradiation

Co-reporter:Shun-Jun Ji, Zhi-Liang Shen, Da-Gong Gu, Shun-Yi Wang

Journal of Organometallic Chemistry 2004 Volume 689(Issue 10) pp:1843-1848

Publication Date(Web):15 May 2004

DOI:10.1016/j.jorganchem.2004.03.006

Michael reactions of deoxybenzoin or dibenzyl ketone with ferrocenyl substituted chalcones catalyzed by sodium hydroxide under ultrasound irradiation can afford the corresponding Michael adducts with excellent yields. It presents a convenient, efficient and simple method for the preparation of ferrocenyl substituted 1,5-diketone compounds in the presence of ultrasound irradiation. In addition, the formation of cyclic, α,β-unsaturated ketones via the reactions of dibenzyl ketone with ferrocenyl substituted chalcones were found, and characterized by X-ray crystal structure analysis.A series of new ferrocenyl substituted 1,5-diketone and cyclic α,β-unsaturated ketones were synthesized in high yields catalyzed by inorganic base under ultrasound irradiation. In addition, influence on the formation of final product between the reactions of dibenzyl ketone and chalcones were investigated.

Study of microwave irradiation polymerization mechanism in the presence of carriers

Co-reporter:Jianmei Lu;Jianfei Wu;Feng Guo;Hui Zhou;Xiulin Zhu

Journal of Applied Polymer Science 2004 Volume 91(Issue 3) pp:1519-1524

Publication Date(Web):25 NOV 2003

DOI:10.1002/app.13334

Microwave irradiation polymerization was studied in the presence of a carrier. The influence of different carriers, such as Al₂O₃, SiO₂, and MgO on the microwave irradiation polymerization mechanism of acrylamide and 2-ethylhexyl acrylate was studied by adopting polymerization inhibitors such as an anionic inhibitor, cationic inhibitor, and radical inhibitor hydroquinone. When the system contains the carriers Al₂O₃ and SiO₂, the polymerization mechanism occurs according to a radical mechanism, but when the system contains MgO, the polymerization mechanism occurs according to not only a radical mechanism but also an anionic polymerization mechanism with superficial grafting occurring. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 91: 1519–1524, 2004

Third-order nonlinear optical properties of polyureas and polyimide synthesized by microwave irradiation

Co-reporter:Jian-Mei Lu;Zhen-Rong Sun;Nai-Yong Chen;Xiu-Lin Zhu;Wei-Ping Shi;Zu-Geng Wang

Journal of Applied Polymer Science 2003 Volume 89(Issue 10) pp:2611-2617

Publication Date(Web):18 JUN 2003

DOI:10.1002/app.12354

Polymerization of benzoguanamine (BGA) and 2,4-tolylenediisocyanate (TDI), BGA–TDI polycondensation polyurea (PU), and pyromellitic dianhydride (PMDA) in solid phase under microwave radiation was studied. In the system of TDI and BGA, the effect of microwave radiation time, the composition and concentration of monomer, the temperature, and the concentration of catalyst on the third-order optical nonlinearities of polymer were discussed. In the system of PU and PMDA, the effect of imidization degree on third-order optical nonlinearities was also discussed. The results showed that the prepared polymer had high third-order nonlinear optical coefficients (PU: χ⁽³⁾ = 1.174 × 10⁻¹³ esu) and fast time responses (24 ps); simultaneously, the third-order optical nonlinearities of polymer were improved greatly by microwave radiation. The results also showed that third-order optical nonlinearities were affected not only by the length of the polycondensate chain but also by the molecular structure, which was explained and confirmed by the computation of the AM1 semiempirical method and UV-visible absorption spectrum. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 2611–2617, 2003

Construction of chiral 3,3-disubstituted oxindoles by a thiourea-catalyzed substitution of phenylsulfonyl with 2-naphthol

Co-reporter:Zhen-Hua Xing, Ying Zhang, Yong Wang, Xiao-Ping Xu, Shun-Jun Ji

Tetrahedron Letters (22 March 2017) Volume 58(Issue 12) pp:1094-1097

Publication Date(Web):22 March 2017

DOI:10.1016/j.tetlet.2017.01.077

Metal-free oxidative direct C(sp3)–H bond functionalization of ethers with α,α-diaryl allylic alcohols

Co-reporter:Xue-Qiang Chu, Hua Meng, You Zi, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2014 - vol. 50(Issue 68) pp:NaN9721-9721

Publication Date(Web):2014/06/27

DOI:10.1039/C4CC04282D

A metal-free method for direct C(sp3)–H bond functionalization of simple ethers with α,α-diaryl allylic alcohols is described. The established protocol provides facile access to α-aryl-β-oxyalkylated carbonyl ketones via radical addition and a 1,2-aryl migration cascade process. An application of the product has been demonstrated in the synthesis of a serotonin antagonist.

tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)–H/C(sp2)–H bond functionalization

Co-reporter:Jia-Jia Cao, Tong-Hao Zhu, Shun-Yi Wang, Zheng-Yang Gu, Xiang Wang and Shun-Jun Ji

Chemical Communications 2014 - vol. 50(Issue 49) pp:NaN6442-6442

Publication Date(Web):2014/02/24

DOI:10.1039/C4CC00743C

An efficient method for the construction of 6-alkyl phenanthridines by tert-butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane was established. Two new C–C bonds were formed in this reaction via a sequential C(sp3)–H/C(sp2)–H bond functionalization under metal-free conditions.

Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration

Co-reporter:Xue-Qiang Chu, You Zi, Hua Meng, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2014 - vol. 50(Issue 57) pp:NaN7645-7645

Publication Date(Web):2014/05/22

DOI:10.1039/C4CC02114B

A novel radical phosphinylation of α,α-diaryl allylic alcohols with arylphosphine oxides was described for the direct preparation of α-aryl-β-phosphinylated carbonyl ketones in medium to good yields via 1,2-aryl migration. In this reaction, formation of new C(Ar)–C(sp3) and C(sp3)–P bonds was observed.

Mn(III)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated phenanthridines

Co-reporter:Jia-Jia Cao, Xiang Wang, Shun-Yi Wang and Shun-Jun Ji

Chemical Communications 2014 - vol. 50(Issue 85) pp:NaN12895-12895

Publication Date(Web):2014/09/01

DOI:10.1039/C4CC05324A

Mn(III)-mediated reactions of 2-isocyanobiaryls with 1,3-dicarbonyl compounds were described for the construction of 6-alkylated and 6-monofluoro-alkylated phenanthridines in moderate to good yields. The reaction involves formation of two new C–C bonds and one C–C bond cleavage.

The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions

Co-reporter:Zheng-Yang Gu, Jia-Jia Cao, Shun-Yi Wang and Shun-Jun Ji

Chemical Science (2010-Present) 2016 - vol. 7(Issue 7) pp:NaN4072-4072

Publication Date(Web):2016/03/11

DOI:10.1039/C6SC00240D

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiazine derivatives via formation of two C–S bonds under transition metal-free, additive-free and oxidant-free conditions. K2S not only provides the sulfur insertion source, but also ignites the reaction through the formation of a trisulfur radical anion and electrons in DMF.

Sulfuration of the C(sp2)–H bond of enaminones: a protocol for the synthesis of thioether using elemental sulfur as a sulfurating reagent

Co-reporter:Li-Fang Yang, Cheng-Guo Liu, Xiao-Ping Xu and Shun-Jun Ji

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 10) pp:NaN2999-2999

Publication Date(Web):2016/02/04

DOI:10.1039/C5OB02619A

Sulfuration reaction of the C(sp2)–H bond of enaminones with elemental sulfur in the presence of CuBr/K3PO4 was carried out. It provided an efficient method for the synthesis of thioethers in moderate to good yields. The protocol was also applicable to synthesize selenides when selenium powder was used instead of sulfur powder.

Synthesis of 1,4-dihydroquinoline derivatives under transition-metal-free conditions and their diverse applications

Co-reporter:Xue-Qiang Chu, You Zi, Hua Meng, Xiao-Ping Xu and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 24) pp:NaN4251-4251

Publication Date(Web):2014/04/22

DOI:10.1039/C4OB00475B

A transition-metal-free process for the synthesis of 1,4-dihydroquinoline derivatives starting from simple enaminones with aldehydes via intermolecular cascade cyclization in a one-pot protocol is developed. This methodology affords a variety of products in moderate to good yields. Particularly, the use of the enaminone fragment in 1,4-dihydroquinoline derivatives 3 as a leaving group for further diverse applications with C-nucleophiles is proved to be feasible.

One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

Co-reporter:Xin-Mou Lu, Jian Li, Zhong-Jian Cai, Rong Wang, Shun-Yi Wang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 46) pp:NaN9477-9477

Publication Date(Web):2014/10/01

DOI:10.1039/C4OB01580K

An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen reaction and cyclization under basic conditions has been reported. The desired products could be obtained in moderate to good yields.

Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

Co-reporter:Rong Wang, Shun-Yi Wang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 11) pp:NaN1740-1740

Publication Date(Web):2014/01/15

DOI:10.1039/C3OB42570C

A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C–C bond cleavage in the presence of water under mild conditions.

Dual 1,3-dipolar cycloaddition of carbon dioxide: two CO bonds of CO2 react in one reaction

Co-reporter:Li-Li Zhao, Shun-Yi Wang, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2013 - vol. 49(Issue 25) pp:NaN2571-2571

Publication Date(Web):2013/01/17

DOI:10.1039/C3CC38526D

The first investigation into two CO bonds of CO2 reacting in one reaction through dual 1,3-dipolar cycloaddition of CO2 with isocyanides and dialkyl acetylenedicarboxylates has been reported. The reaction proceeded efficiently at 80 °C at a pressure of 1 atm of CO2, affording symmetric 1,6-dioxospiro[4,4]nonane-3,8-diene derivatives in moderate yields.

Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines

Co-reporter:Zhong-Jian Cai, Chao Yang, Shun-Yi Wang and Shun-Jun Ji

Chemical Communications 2015 - vol. 51(Issue 75) pp:NaN14270-14270

Publication Date(Web):2015/08/12

DOI:10.1039/C5CC06510K

A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed. This tandem cross-coupling protocol represents a simple, efficient, step- and atom-economic approach for the construction of scarcely known polyene-substituted benzo[d][1,3]oxazines in moderate to excellent yields with a broad substrate scope.

Synthesis of fused indoline heterocycles via dearomatization of indoles with α-bromohydrazones: a systematic study on the substrates

Co-reporter:Wen-Bin Cao, Xiao-Ping Xu and Shun-Jun Ji

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 7) pp:NaN1654-1654

Publication Date(Web):2017/01/06

DOI:10.1039/C6OB02362B

An efficient metal-free dearomatization of indoles with α-bromohydrazones is reported. Various fused indoline heterocycles, which are potentially biologically active, were achieved in good yields (up to 94%) under mild conditions. A systematic study on electronic- and steric effects of substrate and reagents revealed that they have great influence upon the reaction. Based on this, the scope of indoles and α-bromohydrazones was widely exploited.

Copper-catalyzed construction of eight-membered rings via oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines: efficient synthesis of benzo[1,3,5]triazocin-6(5H)-ones

Co-reporter:Wen-Bin Cao, Xue-Qiang Chu, Yu Zhou, Ling Yin, Xiao-Ping Xu and Shun-Jun Ji

Chemical Communications 2017 - vol. 53(Issue 49) pp:NaN6604-6604

Publication Date(Web):2017/05/25

DOI:10.1039/C7CC02815F

Novel and efficient synthesis of eight-membered nitrogen heterocycles in one pot by copper-catalyzed oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines has been described. This protocol features easily available substrates and high step-economy. More importantly, dioxygen as the most ideal oxidant was employed under mild reaction conditions. A variety of valuable benzo[1,3,5]triazocin-6(5H)-one derivatives bearing functional groups were assembled in middle to good yields.

Asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media

Co-reporter:Ying Zhang, Shun-Yi Wang, Xiao-Ping Xu, Ran Jiang and Shun-Jun Ji

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 12) pp:NaN1937-1937

Publication Date(Web):2013/02/01

DOI:10.1039/C3OB00045A

Organocatalyzed asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media has been developed. The reactions proceeded efficiently in the presence of the MacMillan catalyst to give the desired products in good to excellent yields with moderate diastereoselectivities and excellent enantioselectivities.

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