Aijun Lin

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Name: 林爱俊

Organization: China Pharmaceutical University , China

Department: State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry

Title: (PhD)

Chemicals
References

Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes

Co-reporter:Shang Gao, Hao Liu, Chi Yang, Zhiyuan Fu, Hequan Yao, and Aijun Lin

Organic Letters September 15, 2017 Volume 19(Issue 18) pp:

Publication Date(Web):August 24, 2017

DOI:10.1021/acs.orglett.7b01960

An unprecedented palladium-catalyzed allylic alkylation of pronucleophiles with unactivated skipped enynes has been developed. This method provides a straightforward access to a wide array of 1,3-dienes without the need to preinstall leaving groups or employ extra oxidants. The reaction exhibited high atom economy, good functional group tolerance, excellent regioselectivities, and scalability. With D2O as cosolvent, deuterium could be incorporated in high efficiency.

[3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones

Co-reporter:Kaifan Zhang, Xiaoying Xu, Jiuan Zheng, Hequan Yao, Yue Huang, and Aijun Lin

Organic Letters May 19, 2017 Volume 19(Issue 10) pp:

Publication Date(Web):May 9, 2017

DOI:10.1021/acs.orglett.7b00914

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-scale experiments and further derivatization of tetrahydro-β-carbolinones highlighted the potential utility of our method.

Silver-Catalyzed Cascade 1,6-Addition/Cyclization of para-Quinone Methides with Propargyl Malonates: An Approach to Spiro[4.5]deca-6,9-dien-8-ones

Co-reporter:Zhenbo Yuan, Lina Liu, Rui Pan, Hequan Yao, and Aijun Lin

The Journal of Organic Chemistry August 18, 2017 Volume 82(Issue 16) pp:8743-8743

Publication Date(Web):July 18, 2017

DOI:10.1021/acs.joc.7b01400

An unprecedented silver-catalyzed cascade 1,6-addition/5-exo-dig cyclization reaction between para-quinone methides and propargyl malonates under mild reaction conditions has been described. This reaction provides an efficient method to construct versatile spiro[4.5]cyclohexadienones in moderate to excellent yields with high atom economy and scalability.

Palladium-catalyzed Oxa-[4+2] Annulation of para-Quinone Methides

Co-reporter:Zhenbo Yuan;Rui Pan;He Zhang;Lina Liu;Hequan Yao

Advanced Synthesis & Catalysis 2017 Volume 359(Issue 23) pp:4244-4249

Publication Date(Web):2017/12/11

DOI:10.1002/adsc.201700978

AbstractA palladium-catalyzed oxa-[4+2] annulation of para-quinone methides with allyl carbonates bearing a nucleophilic alcohol side chain has been developed. This method provided an efficient strategy to the construction of 2-oxaspiro-cyclohexadienones via 1,6-conjugated addition-mediated allylation in moderate to good yields. Preliminary results on asymmetric derivatives promised potential in the synthesis of enantioenriched frameworks.

Palladium-catalyzed allylic alkylation with internal alkynes to construct C–C and C–N bonds in water

Co-reporter:Shang Gao;Hao Liu;Zijun Wu;Hequan Yao

Green Chemistry (1999-Present) 2017 vol. 19(Issue 8) pp:1861-1865

Publication Date(Web):2017/04/20

DOI:10.1039/C7GC00666G

A palladium-catalyzed system enabled efficient allylic alkylation with alkynes in water has been developed. This reaction presents an environmentally friendly strategy for constructing lots of allylic compounds with indolinones, ketones, amines as well as electron-rich aromatic compounds as nucleophiles. Moreover, the in situ formed arylallene intermediate adopting alkynes as starting materials omits the need for leaving groups and extra oxidants, showing high atom economy. The versatility of the developed reaction also lends itself to the incorporation of deuteriums by simply replacing H2O with D2O.

Cu/Pd cooperatively catalyzed tandem C–N and C–P bond formation: access to phosphorated 2H-indazoles

Co-reporter:Weiwei Wei;Xuanyi Li;Meng Gu;Hequan Yao

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 39) pp:8458-8462

Publication Date(Web):2017/10/11

DOI:10.1039/C7OB02323E

A novel Cu/Pd cooperatively catalyzed tandem C–N and C–P bond formation reaction between 2-alkynyl azobenzenes and P(O)H compounds has been developed. This reaction provides a convenient approach for the synthesis of various phosphorated 2H-indazoles in moderate to good yields, exhibiting good functional group tolerance and high atom economy.

Pd(II)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones

Co-reporter:Xinxin Fang;Shang Gao;Zijun Wu;Hequan Yao

Organic Chemistry Frontiers 2017 vol. 4(Issue 2) pp:292-296

Publication Date(Web):2017/02/01

DOI:10.1039/C6QO00698A

A Pd(II)-catalyzed oxidative Wacker-type cyclization/dearomatization of 2,3-disubstituted indoles with molecular oxygen as the oxidant has been developed. This strategy provides straightforward access to diverse fused indolines bearing C2-oxygenated quaternary stereocenters with good functional group tolerance and high atom economy. Meanwhile, a Pd(II)-catalyzed oxidation/dearomatization of 2-substituted indoles is also presented, which enables the facile synthesis of indolones.

Organocatalyzed [3 + 2] Annulation of Cyclopropenones and β-Ketoesters: An Approach to Substituted Butenolides with a Quaternary Center

Co-reporter:Xuanyi Li, Chunhua Han, Hequan YaoAijun Lin

Organic Letters 2017 Volume 19(Issue 4) pp:

Publication Date(Web):January 30, 2017

DOI:10.1021/acs.orglett.6b03737

An unprecedented organocatalyzed [3 + 2] annulation of cyclopropenones and β-ketoesters has been developed. This reaction provides a direct approach to highly substituted butenolides with a quaternary center in moderate to good yields. The preliminary mechanism study verified that the enol intermediate is crucial to the reaction outcome and the intermolecular esterification and intramolecular Michael addition process were involved.

Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes To Synthesize Indolenines with C3-Quarternary Centers

Co-reporter:Shang Gao, Zijun Wu, Xinxin Fang, Aijun Lin, and Hequan Yao

Organic Letters 2016 Volume 18(Issue 15) pp:3906-3909

Publication Date(Web):July 21, 2016

DOI:10.1021/acs.orglett.6b01947

A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C–H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.

Cooperative Palladium/Proline-Catalyzed Direct α-Allylic Alkylation of Ketones with Alkynes

Co-reporter:Chi Yang, Kaifan Zhang, Zijun Wu, Hequan Yao, and Aijun Lin

Organic Letters 2016 Volume 18(Issue 20) pp:5332-5335

Publication Date(Web):September 29, 2016

DOI:10.1021/acs.orglett.6b02649

The cooperative palladium/l-proline-catalyzed direct α-allylic alkylation of ketones with alkynes is achieved. This reaction exhibits high atom economy since a leaving group is not liberated and a stoichiometric amount of extra oxidant is not needed. A broad range of functional groups are tolerated, and the reaction scope could be further expanded to aldehydes.

Rh(III)-Catalyzed Cascade Annulation/C–H Activation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration

Co-reporter:Songjin Guo, Kai Yuan, Meng Gu, Aijun Lin, and Hequan Yao

Organic Letters 2016 Volume 18(Issue 20) pp:5236-5239

Publication Date(Web):October 5, 2016

DOI:10.1021/acs.orglett.6b02534

A Rh(III)-catalyzed cascade annulation/C–H activation of o-ethynylanilines with diazo compounds has been developed. This concise method allows for the rapid formation of a number of benzo[a]carbazoles in high yields, exhibiting good functional group tolerance and scalability. The key to the success of this approach involves one C–N bond and two C–C bond formation, and an aryl-to-aryl 1,4-rhodium migration.

[3 + 2] Cycloaddition Reaction of in Situ Formed Azaoxyallyl Cations with Aldehydes: An Approach to Oxazolidin-4-ones

Co-reporter:Kaifan Zhang, Chi Yang, Hequan Yao, and Aijun Lin

Organic Letters 2016 Volume 18(Issue 18) pp:4618-4621

Publication Date(Web):August 29, 2016

DOI:10.1021/acs.orglett.6b02254

A novel [3 + 2] cycloaddition reaction between in situ formed azaoxyallyl cations and aldehydes has been developed. This concise method allows the rapid formation of a number of oxazolidin-4-ones in high yields with good functional group tolerance at room temperature. Further transformation and late-stage modifications of drug molecules could also be achieved in good yields, highlighting the potential utility of the reaction.

Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans

Co-reporter:Peng Sun, Shang Gao, Chi Yang, Songjin Guo, Aijun Lin, and Hequan Yao

Organic Letters 2016 Volume 18(Issue 24) pp:6464-6467

Publication Date(Web):December 1, 2016

DOI:10.1021/acs.orglett.6b03355

A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C–H activation/decarbonylation/annulation process, while AcOH led to chromones through a C–H activation/annulation pathway. The reaction exhibited good functional group tolerance and scalability. Moreover, only a single regioisomer of benzofuran was obtained due to the in situ decarbonylation orientation effect.

Bifunctional Organo/Metal Cooperatively Catalyzed [3 + 2] Annulation of para-Quinone Methides with Vinylcyclopropanes: Approach to Spiro[4.5]deca-6,9-diene-8-ones

Co-reporter:Zhenbo Yuan, Weiwei Wei, Aijun Lin, and Hequan Yao

Organic Letters 2016 Volume 18(Issue 14) pp:3370-3373

Publication Date(Web):July 5, 2016

DOI:10.1021/acs.orglett.6b01512

A novel [3 + 2] annulation between para-quinone methides and vinylcyclopropanes for the synthesis of spiro[4.5]deca-6,9-diene-8-ones has been described. The palladium and phosphine–thiourea cooperative catalysis system played an important role in high yields and diastereoselectivities. The reaction exhibited good functional group tolerance and scalability.

Multiple Roles of the Pyrimidyl Group in the Rhodium-Catalyzed Regioselective Synthesis and Functionalization of Indole-3-carboxylic Acid Esters

Co-reporter:Hui Jiang;Shang Gao;Jinyi Xu;Xiaoming Wu;Hequan Yao

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 2) pp:188-194

Publication Date(Web):

DOI:10.1002/adsc.201500769

Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center

Co-reporter:Shang Gao, Chi Yang, Yue Huang, Lei Zhao, Xiaoming Wu, Hequan Yao and Aijun Lin

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 3) pp:840-843

Publication Date(Web):23 Nov 2015

DOI:10.1039/C5OB01970B

A Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved for the first time. The reaction exhibited good functional group tolerance and gram-scale capacity.

1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes

Co-reporter:Shang Gao;Xiuyan Xu;Zhenbo Yuan;Haipin Zhou;Hequan Yao

European Journal of Organic Chemistry 2016 Volume 2016( Issue 17) pp:3006-3012

Publication Date(Web):

DOI:10.1002/ejoc.201600385

A 1,6-addition arylation reaction of para-quinone methides with α-isocyanoacetamides and electron-rich aromatic compounds under metal-free conditions has been developed. BF₃·Et₂O plays two roles in the reaction: catalyzing the cyclization of α-isocyanoacetamides to give oxazoles, and activating the para-quinone methides to achieve the 1,6-addition arylation process. The reaction shows good functional group tolerance, scalability, and regioselectivity. It is a consice protocol for the synthesis of diverse unsymmetrical triarylmethanes. Further transformation of the resulting triarylmethanes provides an efficient route to some functionalized molecules.

Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones

Co-reporter:Youzhi Wu, Peng Sun, Kaifan Zhang, Tie Yang, Hequan Yao, and Aijun Lin

The Journal of Organic Chemistry 2016 Volume 81(Issue 5) pp:2166-2173

Publication Date(Web):January 28, 2016

DOI:10.1021/acs.joc.5b02824

Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.

Rhodium-Catalyzed Hydroacylation of para-Quinone Methides with Salicylaldehydes: An Approach to α,α-Diaryl-2-Hydroxy Acetophenones

Co-reporter:Chi Yang, Shang Gao, Hequan Yao, and Aijun Lin

The Journal of Organic Chemistry 2016 Volume 81(Issue 23) pp:11956-11964

Publication Date(Web):October 28, 2016

DOI:10.1021/acs.joc.6b01859

A rhodium-catalyzed hydroacylation of para-quinone methides (p-QMs) with salicylaldehydes has been disclosed. This method allows for the construction of α,α-diaryl-2-hydroxy acetophenones through tandem C–H activation/C–C bond formation/aromatization process. Moreover, this unprecedented hydroacylation of trisubstituted alkenes exhibits good yields with broad functional group tolerance as well as gram-scale capacity.

Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides

Co-reporter:Kuo Gai, Xinxin Fang, Xuanyi Li, Jinyi Xu, Xiaoming Wu, Aijun Lin and Hequan Yao

Chemical Communications 2015 vol. 51(Issue 87) pp:15831-15834

Publication Date(Web):04 Sep 2015

DOI:10.1039/C5CC06287J

An efficient one-pot approach for the synthesis of spiro[2.5]octa-4,7-dien-6-ones by employing para-quinone methides has been developed. The reaction proceeded smoothly in high yields under mild conditions without the use of metals. Moreover, all products obtained herein contained two or three consecutive quaternary centers.

Synthesis of Heterocycle-fused Pyridine N-Oxides from Oximes and Diazo Compounds via RhIII-Catalyzed CH Activation and Annulation

Co-reporter:Peng Sun;Youzhi Wu;Tie Yang;Xiaoming Wu;Jinyi Xu;Hequan Yao

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 11) pp:2469-2473

Publication Date(Web):

DOI:10.1002/adsc.201500125

Organocatalyzed Formal [4+2] Cycloaddition of in situ Generated Azoalkenes with Arylacetic Acids: An Efficient Approach to the Synthesis of 4,5-Dihydropyridazin-3(2H)-ones

Co-reporter:Xuanyi Li;Kuo Gai;Zhenbo Yuan;Jie Wu;Hequan Yao

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 16-17) pp:3479-3484

Publication Date(Web):

DOI:10.1002/adsc.201500645

1,6-Conjugated Addition-Mediated [2+1] Annulation: Approach to Spiro[2.5]octa-4,7-dien-6-one

Co-reporter:Zhenbo Yuan, Xinxin Fang, Xuanyi Li, Jie Wu, Hequan Yao, and Aijun Lin

The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:11123-11130

Publication Date(Web):October 6, 2015

DOI:10.1021/acs.joc.5b01793

A formal 1,6-conjugated addition-mediated [2+1] annulation to synthesize spiro[2.5]octa-4,7-dien-6-one with p-quinone methides and sulfur ylides has been described. This domino-type process was highly diastereoselective and exhibited good functional group tolerance and scalability without the use of metals and bases.

Solvent-Controlled Switchable C–H Alkenylation of 4-Aryl-1H-pyrrole-3-carboxylates: Application to the Total Synthesis of (±)-Rhazinilam

Co-reporter:Youla Su, Haipin Zhou, Jiaxuan Chen, Jinyi Xu, Xiaoming Wu, Aijun Lin, and Hequan Yao

Organic Letters 2014 Volume 16(Issue 18) pp:4884-4887

Publication Date(Web):September 7, 2014

DOI:10.1021/ol5023933

A solvent-controlled switchable C–H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.

Construction of indoloquinolinones via Pd(II)-catalyzed tandem CC/CN bond formation: application to the total synthesis of isocryptolepine

Co-reporter:Xuebing Chen, Peng Sun, Jinyi Xu, Xiaoming Wu, Lingyi Kong, Hequan Yao, Aijun Lin

Tetrahedron Letters 2014 Volume 55(Issue 51) pp:7114-7117

Publication Date(Web):17 December 2014

DOI:10.1016/j.tetlet.2014.11.008

Construction of indoloquinolinone skeleton via Pd-catalyzed tandem CC/CN bond formation has been achieved in moderate to good yields. The method was applied toward the total synthesis of the bioactive natural product isocryptolepine in good overall yields.

Organocatalyzed Asymmetric 1,6-Conjugate Addition of para-Quinone Methides with Dicyanoolefins

Co-reporter:Xuanyi Li; Xiuyan Xu; Weiwei Wei; Aijun Lin;Hequan Yao

Organic Letters () pp:

Publication Date(Web):January 13, 2016

DOI:10.1021/acs.orglett.5b03471

A chiral thiourea catalyzed asymmetric 1,6-conjugate addition of para-quinone methides with dicyanoolefins has been developed. The reaction provided an efficient approach to the synthesis of chiral diarylmethine skeletons in good yields (up to 99% yield) with high diastereo- and enantioselectivity (>20:1 dr and up to 99.5:0.5 er), also on a gram scale. The preliminary mechanistic study showed that the remote stereocontrol was achieved through intermolecular hydrogen-bond interaction between the chiral thiourea catalyst and the para-quinone methides directly for the first time.

Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides

Co-reporter:Kuo Gai, Xinxin Fang, Xuanyi Li, Jinyi Xu, Xiaoming Wu, Aijun Lin and Hequan Yao

Chemical Communications 2015 - vol. 51(Issue 87) pp:NaN15834-15834

Publication Date(Web):2015/09/04

DOI:10.1039/C5CC06287J

Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center

Co-reporter:Shang Gao, Chi Yang, Yue Huang, Lei Zhao, Xiaoming Wu, Hequan Yao and Aijun Lin

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 3) pp:NaN843-843

Publication Date(Web):2015/11/23

DOI:10.1039/C5OB01970B

Pd(II)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones

Co-reporter:Xinxin Fang, Shang Gao, Zijun Wu, Hequan Yao and Aijun Lin