Yi Pan

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Name: 潘毅

Organization: Nanjing University , China

Department: School of Chemistry and Chemical Engineering

Title: NULL(PhD)

TOPICS

Polymer

Stimuli Responsive Polymers Stimuli Responsive Polymers Photo Responsive Polymers

Chemicals
References

Visible-Light Photoredox Catalyzed Oxidative/Reductive Cyclization Reaction of N-Cyanamide Alkenes for the Synthesis of Sulfonated Quinazolinones

Co-reporter:Ping Qian, Yu Deng, Haibo Mei, Jianlin Han, Jie Zhou, and Yi Pan

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

Publication Date(Web):September 6, 2017

DOI:10.1021/acs.orglett.7b02163

An efficient photocatalytic oxidative/reductive cyclization reaction of N-cyanamide alkenes with arylsulfinic acids or arylsulfonyl chlorides, which proceeds through C–S, C–C, and C–N bond formations, is reported. This photocatalytic reaction was carried out under mild conditions, which provides a new strategy for the synthesis of sulfonated quinazolinones. Furthermore, a one-pot procedure to achieve terminal alkenes has been explored via elimination of the obtained sulfonated quinazolinones under basic conditions.

Access to Alkyl-Substituted Lactone via Photoredox-Catalyzed Alkylation/Lactonization of Unsaturated Carboxylic Acids

Co-reporter:Wanxing Sha, Shengyang Ni, Jianlin Han, and Yi Pan

Organic Letters November 3, 2017 Volume 19(Issue 21) pp:5900-5900

Publication Date(Web):October 17, 2017

DOI:10.1021/acs.orglett.7b02899

An efficient photoredox-catalyzed alkylation/lactonization reaction of unsaturated carboxylic acids by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. Varieties of redox-active esters derived from aliphatic carboxylic acids were proved viable in this method, affording alkyl substituted lactones in moderate to good yields. This redox-neutral procedure features mild conditions and operational simplicity, which provides a new strategy for the synthesis of alkyl substituted lactones.

Detrifluoroacetylative cascade reactions of bicyclic fluoro-enolates with ortho-phthalaldehyde: Aspects of reactivity, diastereo- and enantioselectivity

Co-reporter:Wanxing Sha, Lijun Zhang, Xiaodong Wu, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, Yi Pan

Journal of Fluorine Chemistry 2017 Volume 196(Volume 196) pp:

Publication Date(Web):1 April 2017

DOI:10.1016/j.jfluchem.2016.06.008

The development of new asymmetric methods for preparation of chiral fluorine-containing compounds is in extremely high demand in many areas of chemical research and industry. Herein, we describe a new cascade reaction approach, exemplified by the reactions of, in situ generated fluoro-enolates, with ortho-phthalaldehyde. The reactions proceed through the sequence of detrifluoroacetylation, aldol addition, intramolecular cyclization and oxidation, under convenient conditions with synthetically attractive stereochemical outcome and good structural generality. We demonstrate that these cascade reactions can be performed in catalytic asymmetric mode affording diastereomerically pure products with up to 86% ee.A detrifluoroacetylative cascade reactions between bicyclic 1,3-di-keto-hydrates, fluoro-enolate precursors, with ortho-phthalaldehyde has been developed, which allows preparation of structurally more complex targets with up to 86% ee.Download high-res image (88KB)Download full-size image

Unusual reactivity of fluoro-enolates with dialkyl azodicarboxylates: Synthesis of isatin-hydrazones

Co-reporter:Yi Zhu, Wenzhong Zhang, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, Yi Pan

Journal of Fluorine Chemistry 2017 Volume 203(Volume 203) pp:

Publication Date(Web):1 November 2017

DOI:10.1016/j.jfluchem.2017.06.010

•An unexpected detrifluoroacetylative addition reaction of azodicarboxylates was reported.•The reaction could be conducted under convenient conditions.•A Michael and nucleophilic substitution process was proposed for this transformation.•The method provides a way to biologically important isatin-hydrazones.We report a new reaction cascade allowing preparation of synthetically important isatin-hydrazones by the reaction of detrifluoroacetylatively in situ generated 3-fluoroindolin-2-one enolates with diethyl azodicarboxylates. The reactions take place under operationally convenient conditions featuring synthetically attractive chemical yields. Plausible mechanistic rationale is discussed.An unexpected reaction of detrifluoroacetylatively in situ generated 3-fluoroindolin-2-one enolates with diethyl azodicarboxylates has been reported, which provide a new method for preparation of biologically important isatin-hydrazones.Download high-res image (98KB)Download full-size image

Sunlight-promoted cyclization versus decarboxylation in the reaction of alkynoates with N-iodosuccinimide: easy access to 3-iodocoumarins

Co-reporter:Shengyang Ni, Jia Cao, Haibo Mei, Jianlin Han, Shuhua Li and Yi Pan

Green Chemistry 2016 vol. 18(Issue 14) pp:3935-3939

Publication Date(Web):23 Jun 2016

DOI:10.1039/C6GC01027J

A sunlight-initiated radical conversion of aryl alkynoates to 3-iodocoumarins has been achieved using N-iodosuccinimide as the iodine source without the use of a catalyst or additive. Experimental, X-ray analysis, and computational studies indicate that the reaction under sunlight proceeds through iodination, spirocyclization and ring expansion to form the kinetic product. The sunlight-driven reaction provides a green pathway to especially valuable 3-halocoumarins derivatives.

Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

Co-reporter:Bingnan Du, Ping Qian, Yang Wang, Haibo Mei, Jianlin Han, and Yi Pan

Organic Letters 2016 Volume 18(Issue 16) pp:4144-4147

Publication Date(Web):August 10, 2016

DOI:10.1021/acs.orglett.6b02289

An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.

DBU-promoted cyclization of vinyl isocyanides with ethers via the functionalization of a C(sp3)–H bond for the synthesis of isoquinolines

Co-reporter:Ping Qian, Bingnan Du, Jie Zhou, Haibo Mei, Jianlin Han and Yi Pan

RSC Advances 2015 vol. 5(Issue 80) pp:64961-64965

Publication Date(Web):13 Jul 2015

DOI:10.1039/C5RA11530B

A DBU-promoted cascade functionalization of a C(sp3)–H bond adjacent to oxygen and a radical cyclization reaction of vinyl isocyanides were developed. The reaction was carried out without the use of any metal catalysts or photoredox catalysis, which provides easy access to multi-functionalized isoquinolines.

Cyclization reaction of N-allylbenzothioamide for direct construction of thiazole and thiazoline

Co-reporter:Wei Zhou, Shengyang Ni, Haibo Mei, Jianlin Han, Yi Pan

Tetrahedron Letters 2015 Volume 56(Issue 27) pp:4128-4130

Publication Date(Web):1 July 2015

DOI:10.1016/j.tetlet.2015.05.047

A facile catalyst-free intramolecular cyclization reaction of N-allylbenzothioamide was reported. The reactions with the substrates bearing electron-withdrawing groups afforded thiazoles as products, while thiazolines formed from the reactions with substrates containing electron-donating groups as well as aliphatic substrate. This reaction provides a new access to 2,5-disubstituted thiazoles and thiazolines directly from readily available N-allylbenzothioamide.A facile catalyst-free intramolecular cyclization reaction of N-allylbenzothioamide was developed affording thiazoles and thiazolines as products with good chemical yields. This reaction provides a new access to 2,5-disubstituted thiazoles and thiazolines directly from readily available N-allylbenzothioamide.

Asymmetric synthesis of β-trifluoromethyl-β-amino acids, including highly sterically constrained α,α-dialkyl derivatives

Co-reporter:Yanling Dai, Chen Xie, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, Yi Pan

Tetrahedron 2015 Volume 71(Issue 51) pp:9550-9556

Publication Date(Web):23 December 2015

DOI:10.1016/j.tet.2015.10.071

Reported herein is asymmetric synthesis of β-trifluoromethyl-β-amino acids via Mannich addition reactions between (Ss)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine and lithium enolates of alkyl acetates. In particular, the scope of this approach allows for preparation of the previously illusive, highly sterically constrained α,α-dialkyl-β-trifluoromethyl-β-amino acids. The method affords the target products with good to excellent chemical yields and diastereoselectivities.β-Trifluoromethyl-β-amino acids, including highly sterically constrained α,α-dialkyl-β-trifluoromethyl-β-amino acids, were synthesized via asymmetric Mannich addition reactions between (Ss)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine and lithium enolates of alkyl 2,2-(dialkyl)acetates.

Asymmetric synthesis of (3S,1′S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

Co-reporter:Ping Qian, Chen Xie, Lingmin Wu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 40) pp:7909-7913

Publication Date(Web):02 Sep 2014

DOI:10.1039/C4OB01453G

This paper presents the first study of the addition reactions between amide-derived nucleophiles and chiral CF3-containing N-sulfinyl-imines. We demonstrate that enolates of 1-(alkyl)-indolin-2-ones cleanly react with (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine affording 3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-ones of (3S,1′S) absolute configuration as the major reaction products with synthetically meaningful diastereoselectivity and chemical yields. The reactions were shown to be of general practical application for preparation of various oxindole derivatives in a diastereomerically pure form.

LDA-promoted asymmetric synthesis of β-trifluoromethyl-β-amino indanone derivatives with virtually complete stereochemical outcome

Co-reporter:Chen Xie, Haibo Mei, Lingmin Wu, Vadim A. Soloshonok, Jianlin Han and Yi Pan

RSC Advances 2014 vol. 4(Issue 9) pp:4763-4768

Publication Date(Web):25 Nov 2013

DOI:10.1039/C3RA45773G

We demonstrate that reactions between various 1-indanones and (SS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine, conducted in the presence of catalytic amounts of LDA, occur with virtually complete stereochemical outcome, offering reliable and generalized access to biologically relevant β-trifluoromethyl-β-amino indanone derivatives. The products can be isolated in diastereomerically pure form simply by washing the crude reaction mixture with hexanes, underscoring practicality of the present method.

Asymmetric synthesis of β′-amino-α,β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines

Co-reporter:Yiwen Xiong, Haibo Mei, Jianlin Han, Guigen Li, Yi Pan

Tetrahedron Letters 2014 Volume 55(Issue 15) pp:2476-2479

Publication Date(Web):9 April 2014

DOI:10.1016/j.tetlet.2014.03.005

Efficient asymmetric Mannich addition reactions between α,β-unsaturated ketone derived enolates and N-phosphonyl imines were reported. These reactions could proceed smoothly for a variety of imine substrates with good (up to 96%) chemical yields and excellent diastereoselectivities (up to 98:2 dr). The method reported in this work provides an easy access to chiral β′-amino-α,β-enones.

Operationally convenient method for preparation of sulfonamides containing α,α-difluoro-β-amino carbonyl moiety

Co-reporter:Chen Xie, Lingmin Wu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han, Yi Pan

Tetrahedron Letters 2014 Volume 55(Issue 43) pp:5908-5910

Publication Date(Web):22 October 2014

DOI:10.1016/j.tetlet.2014.09.001

We report here that the reactions of in situ generated unprotected α,α-difluoroenolates with various N-sulfonyl imines take place under operationally convenient conditions affording a novel type of fluorinated sulfonamides of high pharmaceutical potential. The reactions feature structural generality, excellent yields and can be easily scaled up for practical preparation of the target fluorine-containing sulfonamides.A new efficient reaction between in situ generated unprotected α,α-difluoroenolates with various N-sulfonyl imines was reported, which was carried out under operationally convenient conditions affording a novel type of fluorinated sulfonamides of high pharmaceutical potential with excellent chemical yields.

N,N-Diisopropyl-N-phosphonyl imines lead to efficient asymmetric synthesis of aziridine-2-carboxylic esters

Co-reporter:Padmanabha V. Kattamuri, Yiwen Xiong, Yi Pan and Guigen Li

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 20) pp:3400-3408

Publication Date(Web):19 Mar 2013

DOI:10.1039/C3OB40251G

Highly diastereoselective asymmetric synthesis of chiral aziridine-2-carboxylic esters is reported for 20 examples with good yields (51–87%) and excellent diastereoselectivities (>99:1 dr for most cases). The modified N-phosphonyl imines have proven to be superior to previous imine auxiliaries for the aza Darzens reaction by using a secondary isopropyl group to replace the primary benzyl group for N,N-diamino protection. In the meanwhile, a special operation by slowly adding the pre-cooled imine solution at −78 °C into the preformed β-bromo lithium enolate mixture at this temperature in the presence of 4 Å molecular sieves was found to be crucial in terms of yields and diastereoselectivity. The present method can provide an easy and general access to β-hydroxy α-amino acids and other important amino building blocks.

Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine

Co-reporter:Haibo Mei, Chen Xie, Lingmin Wu, Vadim A. Soloshonok, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 46) pp:8018-8021

Publication Date(Web):17 Oct 2013

DOI:10.1039/C3OB41785A

Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine were found to proceed with reasonably good yields (55%–79%) and exceptionally high stereoselectivity (>99:1 dr). This method presents a general approach for the preparation of a new type of biologically relevant compounds containing pharmacophoric imidazo[2,1-b]thiazole and (trifluoro)ethylamine groups.

Asymmetric Morita–Baylis–Hillman reaction of isatins with α,β-unsaturated γ-butyrolactam as the nucleophile

Co-reporter:Zhiqiang Duan, Zirui Zhang, Ping Qian, Jianlin Han and Yi Pan

RSC Advances 2013 vol. 3(Issue 26) pp:10127-10130

Publication Date(Web):07 May 2013

DOI:10.1039/C3RA41115J

α,β-Unsaturated γ-butyrolactam was reported as the nucleophile for the asymmetric Morita–Baylis–Hillman reaction for the first time. This enantioselective MBH reaction, promoted by chiral bisthiourea with isatins as the electrophile, was carried out under mild conditions, resulting in 3-hydroxyl-2-oxindole derivatives in good to excellent yields and up to 78% ee.

Asymmetric CC Bond Formation between Chiral N-Phosphonyl Imines and a Nickel(II)-Complexed Glycine Schiff Base Provides Efficient Synthesis of ,-syn-Diamino Acid Derivatives

Co-reporter:Hao Sun;Haowei Zhang;Jianlin Han;Guigen Li

European Journal of Organic Chemistry 2013 Volume 2013( Issue 22) pp:4744-4747

Publication Date(Web):

DOI:10.1002/ejoc.201300554

Abstract

The group-assisted purification asymmetric synthesis of α,β-diamino acid derivatives was achieved by treating chiral N-phosphonyl imines with a Ni^II-complexed glycine-derived enolate; traditional purification techniques such as chromatography and recrystallization are not required. Successful control of the syn stereochemistry of the vicinal diamino products complements our previous methods that afforded anti stereoisomers; thus, all four individual isomers can be synthesized simply by changing the geometry of the enolate. In contrast to our previous synthesis in which at least 5 equiv. of the glycine Schiff base enolate was required for complete conversion, the new synthesis only needs 1.1 equiv. of the glycine Schiff base enolate to give complete diastereoselectivity (>30:1 dr) and high yields (91–97 %). The absolute stereochemistry was unambiguously determined by X-ray structure analysis.

Highly diastereoselective aminobromination of β-methyl-β-nitrostyrenes with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources

Co-reporter:Sheng Chen, Jianlin Han, Guigen Li, Yi Pan

Tetrahedron Letters 2013 Volume 54(Issue 22) pp:2781-2784

Publication Date(Web):29 May 2013

DOI:10.1016/j.tetlet.2013.02.113

A facile and stereoselective aminobromination reaction of α,β-unsaturated nitro compounds with t-butyl N,N-dibromocarbamate/t-butyl carbamate as bromine/nitrogen sources was reported. This catalytic system could tolerate a wide scope of β-methyl-β-nitrostyrenes, resulting in good chemical yields and excellent regio- and stereoselectivities. Furthermore, the N-t-butoxycarbonyl protecting group could be easily cleaved to afford the free vicinal haloamines.A highly regio- and stereoselective aminobromination of β-methyl-β-nitrostyrenes with K3PO4 as catalyst and BocNH2/BocNBr2 as nitrogen/bromine has been established. The N-protecting group was removed under simple and mild condition, giving free bromoamines.

Iron-catalyzed alkenylation of cyclic ethers via decarboxylative sp3(C)–sp2(C) coupling

Co-reporter:Jincan Zhao, Wei Zhou, Jianlin Han, Guigen Li, Yi Pan

Tetrahedron Letters 2013 Volume 54(Issue 48) pp:6507-6510

Publication Date(Web):27 November 2013

DOI:10.1016/j.tetlet.2013.09.082

An efficient Fe(acac)3-catalyzed decarboxylative C(sp2)–C(sp3) coupling reaction via oxidation of C–H bond adjacent to an oxygen atom has been developed successfully, in which cyclic ethers are selectively transformed into the corresponding alkenylation products with good chemical yields and excellent stereoselectivities. The mechanism was studied and the reaction was supposed to proceed through a radical oxidative coupling process.An efficient Fe(acac)3-catalyzed decarboxylative C(sp2)–C(sp3) coupling reaction has been reported, in which cyclic ethers are selectively transformed into corresponding alkenylation products with good chemical yields and excellent stereoselectivities.Figure optionsDownload full-size imageDownload as PowerPoint slide

Approach to Vicinal t-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization

Co-reporter:Hao Sun, Jianlin Han, Padmanabha V. Kattamuri, Yi Pan, and Guigen Li

The Journal of Organic Chemistry 2013 Volume 78(Issue 3) pp:1171-1175

Publication Date(Web):January 11, 2013

DOI:10.1021/jo302727v

A 1.0 mol % amount of K3PO4·3H2O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. Anew mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.

Catalyst-Free Intramolecular Oxidative Cyclization of N-Allylbenzamides: A New Route to 2,5-Substituted Oxazoles

Co-reporter:Wei Zhou, Chen Xie, Jianlin Han, and Yi Pan

Organic Letters 2012 Volume 14(Issue 18) pp:4766-4769

Publication Date(Web):August 30, 2012

DOI:10.1021/ol302031z

A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easily accessible substrates under temperate conditions.

Na3PO4-catalyzed aminochlorination reaction of β-nitrostyrenes in water

Co-reporter:Haibo Mei, Yiwen Xiong, Yu Qian, Jianlin Han, Guigen Li and Yi Pan

RSC Advances 2012 vol. 2(Issue 1) pp:151-155

Publication Date(Web):27 Oct 2011

DOI:10.1039/C1RA00679G

A facile and green aminochlorination of β-nitrostyrenes has been developed by using t-butyl N,N-dichlorocarbamate (BocNCl2) as a nitrogen/chlorine source in water at room temperature, which tolerated a wide range of substrates and resulted in the highest efficiency so far.

Highly regioselective aminobromination of α,β-unsaturated nitro compounds with benzyl carbamate/N-bromosuccinimide as nitrogen/bromine source

Co-reporter:Xiaoyun Ji, Zhiqiang Duan, Yu Qian, Jianlin Han, Guigen Li and Yi Pan

RSC Advances 2012 vol. 2(Issue 13) pp:5565-5570

Publication Date(Web):04 Apr 2012

DOI:10.1039/C2RA20490H

Aminobromination of α,β-unsaturated nitro compounds with benzyl carbamate and N-bromosuccinimide as nitrogen/bromine sources was reported. This new catalytic system tolerates a wide range of aromatic substrates, as well as heterocyclic and aliphatic substrates, resulting in good chemical yields. The reaction also proceeds smoothly with water as a medium in high efficiency. This practical aminobromination method was also proved to be suitable for large-scale preparation. Furthermore, the N-carbobenzoxy protecting group could be easily cleaved to afford the free vicinal haloamines.

Tandem 1,5-migration/Michael reactions to prepare adducts of pyrazolone derivatives: protecting group-directed rearrangement

Co-reporter:Zhijin Lu, Chen Xie, Jianlin Han and Yi Pan

RSC Advances 2012 vol. 2(Issue 24) pp:8949-8952

Publication Date(Web):15 Aug 2012

DOI:10.1039/C2RA21549G

A tandem 1,5-migration/Michael reaction of pyrazoline has been described, which results in different multiply-substituted pyrazolone derivatives with excellent yields controlled by protecting group.

Cinchona Alkaloid-catalyzed Asymmetric Direct Mannich Reaction of Malononitrile to Imine for Synthesis of -Amino Malononitrile

Co-reporter:Zhijin Lu;Chen Xie;Wei Zhou;Zhiqiang Duan;Jianlin Han

Chinese Journal of Chemistry 2012 Volume 30( Issue 10) pp:2333-2337

Publication Date(Web):

DOI:10.1002/cjoc.201200586

Abstract

The first direct asymmetric Mannich reaction of malononitrile to N-Boc-protected imines has been developed with cinchona alkaloid as catalyst. The procedure could tolerate a relatively wide range of substrates, and results in excellent yields and good enantioselectivities even in the presence of only 1 mol% of catalyst loading. The present work provides an easy access to β-amino malononitrile derivatives.

A facile organocatalyzed Michael addition of pyrazolines to α,β-unsaturated carbonyl compounds

Co-reporter:Chen Xie, Zhijin Lu, Wei Zhou, Jianlin Han, Yi Pan

Tetrahedron Letters 2012 Volume 53(Issue 49) pp:6650-6653

Publication Date(Web):5 December 2012

DOI:10.1016/j.tetlet.2012.09.096

A new highly efficient cascade reaction of pyrazolines with α,β-unsaturated carbonyl compounds catalyzed by DBU was reported. The process underwent the first deprotection/Michael addition reaction to give 4-substituted pyrazoline derivatives, which were further converted into 4,4-di-substituted pyrazolone derivatives through the second deprotection/Michael reaction. The mechanism for this reaction was also studied.A new highly efficient cascade reaction was reported, which proceeded through two steps of deprotection/Michael. This reaction could tolerate a wide scope of pyrazoline derivatives and α,β-unsaturated carbonyl compounds, giving mono- and bis-substituted-5-pyrazoline derivatives with moderate chemical yields.

Aminochlorination reaction with N-chlorophthalimide as a new nitrogen/chlorine source resulting in α-amino derivatives

Co-reporter:Yu Qian, Xiaoyun Ji, Wei Zhou, Jianlin Han, Guigen Li, Yi Pan

Tetrahedron 2012 68(31) pp: 6198-6203

Publication Date(Web):

DOI:10.1016/j.tet.2012.05.066

Hydrogen-bonding self-assembly of two dimensional (2D) layer structures generating metal–organic nanotubes

Co-reporter:Hailong Sun, Haibo Mei, Guanghui An, Jianlin Han and Yi Pan

CrystEngComm 2011 vol. 13(Issue 3) pp:734-737

Publication Date(Web):30 Nov 2010

DOI:10.1039/C0CE00471E

Two metal–organic nanotubular architectures are built from 2D layer structures with big windows through hydrogen-bonding self-assembly of a thiourea group, representing a strategy for the preparation of metal–organic nanotubes generated from 2D layer structures.

A facile process for the asymmetric synthesis of β-trifluoromethylated β-amino ketonesvia addition of ketone enolates to sulfinylimine

Co-reporter:Haibo Mei, Yiwen Xiong, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 5) pp:1402-1406

Publication Date(Web):05 Jan 2011

DOI:10.1039/C0OB00586J

An efficient method for the asymmetric synthesis of β-trifluoromethylated β-amino ketonesvia addition of ketone-derivative enolates to trifluoromethylated sulfinylimine has been developed, with good chemical yields and excellent diastereoselectivities. This practical method was also proved to be suitable for large-scale preparation.

Ligand-free palladium-catalyzed intramolecular Heck reaction of secondary benzylic bromides

Co-reporter:Wei Zhou, Guanghui An, Guangqian Zhang, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 16) pp:5833-5837

Publication Date(Web):27 May 2011

DOI:10.1039/C1OB05231D

A facile ligand-free palladium-catalyzed intramolecular Heck reaction of β-hydrogen-containing secondary benzylic bromides was developed, which affords pyrroline derivatives with good regioselectivities.

KOH-catalyzed highly efficient aminohalogenation of β-nitrostyrenes with t-butyl N,N-dichlorocarbamate as nitrogen/halogen source

Co-reporter:Haibo Mei, Jianlin Han, Guigen Li and Yi Pan

RSC Advances 2011 vol. 1(Issue 3) pp:429-433

Publication Date(Web):09 Aug 2011

DOI:10.1039/C1RA00174D

A highly efficient and facile aminohalogenation of β-nitrostyrenes with t-butyl N,N-dichlorocarbamate (BocNCl2) as nitrogen/halogen source is reported, which tolerated a wide scope of substrates and could be completed within 20 min at room temperature with excellent chemical yields.

Tetrabenzylhafnium as a New Organometallic Reagent for Imine Addition Resulting in -Branched Amines

Co-reporter:Haibo Mei;Xiaoyun Ji;Jianlin Han

European Journal of Organic Chemistry 2011 Volume 2011( Issue 29) pp:5783-5786

Publication Date(Web):

DOI:10.1002/ejoc.201100820

Abstract

Tetrabenzylhafnium has been explored as a new organometallic reagent for the imine addition reaction. This reagent tolerates a wide scope of imines, affording α-branched amines in excellent yields without the use of any additive or catalyst. This new reagent shows higher efficiency than that observed for classic Grignard and organolithium reagents.

Palladium-Catalyzed Tandem Diperoxidation/C−H Activation Resulting in Diperoxy-oxindole in Air

Co-reporter:Guanghui An, Wei Zhou, Guangqian Zhang, Hao Sun, Jianlin Han, and Yi Pan

Organic Letters 2010 Volume 12(Issue 20) pp:4482-4485

Publication Date(Web):September 14, 2010

DOI:10.1021/ol101664y

A highly efficient and facile palladium-catalyzed tandem diperoxidation and C−H activation process was reported, which provides a new pathway for the synthesis of biologically active diperoxides as well as oxindole derivatives from readily available starting materials in excellent chemical yields.

New catalytic system for aminohalogenation of β-methyl-β-nitrostyrenes to give opposite regiochemistry

Co-reporter:San-Jun Zhi, Hao Sun, Guangqian Zhang, Guigen Li and Yi Pan

Organic & Biomolecular Chemistry 2010 vol. 8(Issue 3) pp:628-631

Publication Date(Web):2009/12/07

DOI:10.1039/B914944A

A new combination of catalyst and co-additive has been found for aminohalogenation reaction of β-methyl-β-nitrostyrenes with N,N-dichloro-p-tolunesulfonamide (4-TsNCl2). The reaction was achieved by using MnSO4 as the catalyst together with tolunesulfonamide to give vicinal haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature under nitrogen atmosphere to give useful to good yields and excellent regio and stereoselectivity. A mechanism involving the formation of chloronium intermediate was proposed to explain the resulting regio and stereochemistry.

Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

Co-reporter:Parminder Kaur, Gaurav Shakya, Hao Sun, Yi Pan and Guigen Li

Organic & Biomolecular Chemistry 2010 vol. 8(Issue 5) pp:1091-1096

Publication Date(Web):05 Jan 2010

DOI:10.1039/B923914F

A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

Copper-catalyzed aminobromination/elimination process: an efficient access to α,β-unsaturated vicinal haloamino ketones and esters

Co-reporter:Hao Sun, Guangqian Zhang, Sanjun Zhi, Jianlin Han, Guigen Li and Yi Pan

Organic & Biomolecular Chemistry 2010 vol. 8(Issue 19) pp:4236-4239

Publication Date(Web):13 Aug 2010

DOI:10.1039/C0OB00283F

A novel copper-catalyzed aminobromination-elimination process has been developed, which provides an easy access to α,β-unsaturated vicinal haloamindes derivatives from readily available α,β-unsaturated ketones and esters in good to excellent yields. The isolated intermediate discloses that the current system proceeds through the aminobromination process.

One-Pot Highly Stereoselective Synthesis of Cyano Aziridines via the CuCl-Catalyzed Aminochlorination of ,-Unsaturated Nitriles and Intramolecular SN2 Substitution

Co-reporter:Haibo Mei;Lijun Yan;Jianlin Han;Guigen Li

Chemical Biology & Drug Design 2010 Volume 76( Issue 5) pp:392-396

Publication Date(Web):

DOI:10.1111/j.1747-0285.2010.01023.x

An efficient one-pot system has been developed for the synthesis of cyano aziridine by using α,β-unsaturated nitriles as the alkene substrates and N,N-dichloro-p-toluenesulfonamide (4-TsNCl₂) as the nitrogen source. A good scope of alkene substrates was achieved for this reaction. The one-pot reaction, via aminohalogenation and intramolecular S_N2 substitution, was very convenient to carry out at room temperature without the protection of inert gases. Modest to good yields and excellent have been obtained. This method provides an easy route to the cyano aziridine. The structure of the resulting products has been unambiguously confirmed by X-ray structural analysis.

The Mimic of Type II Aldolases Chemistry: Asymmetric Synthesis of -Hydroxy Ketones by Direct Aldol Reaction

Co-reporter:Zhijin Lu;Haibo Mei;Jianlin Han

Chemical Biology & Drug Design 2010 Volume 76( Issue 2) pp:181-186

Publication Date(Web):

DOI:10.1111/j.1747-0285.2010.00998.x

An efficient direct aldol reaction has been developed for the synthesis of chiral β-hydroxy ketone using a combination of C₁-symmetric chiral prolinamides based on o-phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts.

Highly Regio- and Stereoselective Synthesis of -(N-Alkyl-N-p-toluenesulfonyl)--Bromo-Ketones via Ni(OAc)2-Catalyzed Aminobromination of Chalcones

Co-reporter:Hao Sun;San-Jun Zhi;Jian-Lin Han;Guigen Li

Chemical Biology & Drug Design 2010 Volume 75( Issue 3) pp:269-276

Publication Date(Web):

DOI:10.1111/j.1747-0285.2010.00938.x

The combinations of N-methyl-p-toluenesulfonamide/NBS and N-ethyl-p-toluenesulfonamide/NBS were found to be good nitrogen/halogen resources for the aminohalogenation of α,β-unsaturated ketones in the presence of Ni(OAc)₂ as the catalyst for the synthesis of vicinal haloamino ketone derivatives. The introduction of N-alkyl groups to the nitrogen resources resulted in excellent regio- and stereoselectivity for both electron-donating and electron-withdrawing group-attached unsaturated ketone substrates. The structure of the resulting products has been unambiguously confirmed by X-ray crystal structure analysis.

The combination of TsNBr2/TsNH2 as the nitrogen/halo source for the aminobromination of β-methyl-β-nitrostyrenes catalyzed by Mn(OAc)2

Co-reporter:Sanjun Zhi, Guanghui An, Hao Sun, Jianlin Han, Guigen Li, Yi Pan

Tetrahedron Letters 2010 Volume 51(Issue 20) pp:2745-2747

Publication Date(Web):19 May 2010

DOI:10.1016/j.tetlet.2010.03.060

The combination of N,N-dibromo-p-tolunesulfonamide (4-TsNBr2) and TsNH2 was found to be an efficient halogen/nitrogen source for the aminohalogenation of β-methyl-β-nitrostyrenes with manganese (II) acetate as the catalyst in the presence of 4 Å molecular sieves. The reaction results in vicinal bromoamino nitroalkanes with the opposite regioselectivity comparing with those reported, which was also confirmed by X-ray structural analysis.The combination of TsNBr2/TsNH2 was found to be an efficient nitrogen/halo source for the aminohalogenation of β-methyl-β-nitrostyrenes resulting in vicinal bromoamino nitroalkanes.

Chiral N-phosphoryl imines: design, synthesis and direct asymmetric addition reactions with diketones and diesters

Co-reporter:Hao Sun, Trideep Rajale, Yi Pan, Guigen Li

Tetrahedron Letters 2010 Volume 51(Issue 33) pp:4403-4407

Publication Date(Web):18 August 2010

DOI:10.1016/j.tetlet.2010.06.072

Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62%—quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.(S)-BINOL-based chiral N-phosphoryl imines have been designed and synthesized. These N-phosphoryl imines have been proven to be efficient for direct 1,2-addition reaction with both cyclic and linear diketones without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. The absolute configuration has been unambiguously determined by converting a product into an authentic sample.

Molecular ladders with finite arms: The first 1D→2D polythreading with finite components based on flexibly long ligand

Co-reporter:Hailong Sun, Zhijin Lu, Jianlin Han, Yi Pan

Inorganic Chemistry Communications 2010 Volume 13(Issue 10) pp:1131-1133

Publication Date(Web):October 2010

DOI:10.1016/j.inoche.2010.06.024

The reactions of MII nitrate (M = Co, Ni) with 1, 4-bis(imidazol-1-ylmethyl) benzene (bix) gave two novel interesting coordination networks [M2(bix)3(NO3)4]. The network contains 1D zigzag molecular ladder motifs, with anionic co-ligand NO3− as side arms on both sides, which thread through the squares of adjacent polymeric units in a mutual relationship, resulting in the first 1D→2D polythreading with finite components based on flexibly long ligand.The first 1D→2D polythreading with finite components based on flexibly long ligand was hydrothermally synthesized and the diffuse reflectance UV–vis spectrum suggests that they may be excellent candidates for potential photoactive materials.

Modified thiourea used as the ligand for the synthesis of novel coordination polymers: Based on its significant conformational behavior and H-bonding preference

Co-reporter:Hailong Sun, Haibo Mei, Chen Xie, Zhijin Lu, Jianlin Han, Yi Pan

Inorganic Chemistry Communications 2010 Volume 13(Issue 11) pp:1361-1365

Publication Date(Web):November 2010

DOI:10.1016/j.inoche.2010.07.037

Modified thiourea was used as the ligand for the synthesis of three novel coordination complexes, basing on its increased H-bond donor ability of the NH group and decreased H-bond acceptor ability of the C = S bond. Complex 1 is the first 3D network with 1D rod SBU and 2D surface SBU based on the long biscarboxylate ligand; Complex 2 has a 2D layer constructed by 1D chains via H-bonds, which shows a “plywood-like array” with a new AABB type; Complex 3 is a 3-fold interpenetrating 5-connected net with the rare 4664 topology.Complex 1 is the first 3D network which has 1D rod SBU and 2D surface SBU based on the long biscarboxylate ligand. Complex 2 shows a “plywood-like array” with a new AABB type. Complex 3 is the first example of 3-fold interpenetrating 5-connected net with a rare 4664 topology.

Catalyst-free aminobromination of alkenes with N-methyl-p-toluenesulfonamide as nitrogen resource

Co-reporter:Guangqian Zhang, Guanghui An, Jun Zheng, Yi Pan, Guigen Li

Tetrahedron Letters 2010 Volume 51(Issue 6) pp:987-989

Publication Date(Web):10 February 2010

DOI:10.1016/j.tetlet.2009.12.059

A catalyst-free electrophilic aminobromination system was described with N-methyl-p-toluenesulfonamide (p-TsNHCH3) and N-bromosuccinimide (NBS) as nitrogen and bromine resources. The reaction can give vicinal haloamines in good yields, excellent regioselectivities, and stereoselectivities under convenient and mild condition. The existence of N-methyl group in the nitrogen resource was found to play an important role in the formation of vicinal haloamine product.A catalyst-free aminohalogenation system was reported with N-methyl-p-toluenesulfonamide as nitrogen resource.

Surface Cobalt Silicate and CoO x Cluster Anchored to SBA-15: Highly Efficient for Cyclohexane Partial Oxidation

Co-reporter:Li Li;Hui Li;Chen Jin;Xiaochen Wang;Weijie Ji

Catalysis Letters 2010 Volume 136( Issue 1-2) pp:20-27

Publication Date(Web):2010 May

DOI:10.1007/s10562-010-0318-z

The present investigation showed that the surface cobalt silicate and CoOx cluster anchored to SBA-15 are highly efficient heterogeneous catalysts for the cyclohexane partial oxidation with air-like O2 (20%)-N2 (80%) mixture as oxidant in the continuously stirred tank reactor at 413 K and 1.0 MPa. Typically, selectivity of 84.6% at cyclohexane conversion of 14.5% can be achieved in a period of 2 h reaction. The performance of Co-catalyst is affected by the nature of Co species introduced to SBA-15. The surface cobalt silicate with higher proportion of “isolated” Co2+ sites shows better result than the well dispersed CoOx clusters mainly on the internal surface of SBA-15. Furthermore, different preparation method also influences the porosity of SBA-15 and accessibility to Co sites, which may in turn affect on the reaction performance.

The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

Co-reporter:SanJun Zhi;HaiBo Mei;GuangQian Zhang;Hao Sun;JianLin Han

Science China Chemistry 2010 Volume 53( Issue 9) pp:1946-1952

Publication Date(Web):2010 September

DOI:10.1007/s11426-010-4001-4

The combination of benzamide and NCS was found to be an efficient nitrogen/halogen source for aminohalogenation of β-nitrostyrenes. The reaction was convenient to carry out by using 4-dimethylaminopyridine as the catalyst, resulting in vicinal dichlorinated haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature with good yields and excellent regioselectivities. A mechanism involving a chloronium intermediate was proposed to explain the resulting regiochemistry. The current system explored a new type of nitrogen sources for aminohalogenation of functionalized olefins.

Zinc-prolinamide complex catalyzed direct asymmetric aldol reactions in the presence of water

Co-reporter:ZhiJin Lu;HaiBo Mei;GuangQian Zhang;JianLin Han

Science China Chemistry 2010 Volume 53( Issue 11) pp:2291-2296

Publication Date(Web):2010 November

DOI:10.1007/s11426-010-4069-x

An efficient direct asymmetric aldol reaction with zinc triflate and prolinamides as combined catalysts is reported. A series of chiral prolinamides have been designed and used in the direct aldol reaction resulting in the desired products with excellent yields (up to 94% yield) and high enantioselectivities (up to 96% ee). Water was found to play a significant role in the formation of the aldol products, which suggests a new strategy in the design of new organic catalysts.

Regioselective aminohalogenation of β-nitrostyrenes using NCS and NBS as nitrogen/halogen sources

Co-reporter:SanJun Zhi;Hao Sun;Chen Lin;GuangQian Zhang;GuiGen Li

Science China Chemistry 2010 Volume 53( Issue 1) pp:140-146

Publication Date(Web):2010 January

DOI:10.1007/s11426-010-0028-9

Aminohalogenation reaction of β-nitrostyrenes with N-halosuccinimides (N-chloro and N-bromosuccinimides) has been successfully conducted by using nickel acetate as a catalyst in the presence of potassium carbonate and succinimide as co-additives. The reaction was easily performed at room temperature under nitrogen gas protection to give dihalorinaed haloamino products in good to excellent yields (60%–98%). The structure has been confirmed by X-ray crystal structure analysis.

Cyclohexane Oxidation Over Size-Uniform Au Nanoparticles (SBA-15 hosted) in a Continuously Stirred Tank Reactor Under Mild Conditions

Co-reporter:Li Li;Chen Jin;Xiaochen Wang;Weijie Ji;Theo van der Knaap

Catalysis Letters 2009 Volume 129( Issue 3-4) pp:303-311

Publication Date(Web):2009 May

DOI:10.1007/s10562-009-9853-x

Cyclohexane oxidation was operated in a continuously stirred tank reactor at system pressures of 0.6–1.0 MPa under an air-like O2/N2 atmosphere (rather than pure O2). Catalytic performance was investigated over Au nanoparticles (size: 3–8 nm) hosted by SBA-15 as well as Au particles (>60 nm) deposited on MCM-41, and high turnover frequencies of desired products were detected over the former. Based on intrinsic activities of representative catalysts, we derived a size-sensitivity feature of cyclohexane oxidation over Au particles.

Selective Reduction of 7-Demethylsinomenine

Co-reporter:Yu-feng LI, Qing-min BU, Yi QIAN, Yi PAN, Jian-xin LI, Le-qun HUANG, Hong-jun ZHU

Chemical Research in Chinese Universities 2008 Volume 24(Issue 5) pp:557-560

Publication Date(Web):September 2008

DOI:10.1016/S1005-9040(08)60117-8

Abstract

Several borohydride reagents: sodium borohydride, sodium cyanoborohydride, soudium acetoxyborohydride and soudium triacetoxyborohydride were screened, respectively, for the reduction of 7-demethylsinomenine, which was an α,β-dicarbonyl compound derived from sinomenine. Highly regio- and stereo-selectivity was acquired when sodium cyanoborohydride or NaBH(OAc)₃ was used. The product was structurally confirmed as 7R configuration by NMR, X-ray crystal diffraction analysis. Some preliminary discussion was also made on the mechanism of the selective reduction.

Synthesis and electroluminescent properties of Ir complexes with benzo[c]acridine or 5,6-dihydro-benzo[c]acridine ligands

Co-reporter:Chunxiang Li, Peipei Sun, Lijun Yan, Yi Pan, Chien-Hong Cheng

Thin Solid Films 2008 Volume 516(Issue 18) pp:6186-6190

Publication Date(Web):31 July 2008

DOI:10.1016/j.tsf.2007.11.094

Two red emitting iridium complexes (DBA)2Ir(acac) and (BA)2Ir(acac) (DBA = 5,6-dihydro-benzo[c]acridine, BA = benzo[c]acridine, acac = acetylacetone) were synthesized. Organic light-emitting devices using these complexes as dopant emitters have been fabricated. The results showed that these complexes have strong phosphorescent characters and the devices emit pure red light. The maximum brightness of the device based on (DBA)2Ir(acac) is 9540 cd/m2 with an external quantum efficiency of 4.66%.

Unprecedented interweaving of single-helical and unequal double-helical chains into chiral metal–organic open frameworks with multiwalled tubular structures

Co-reporter:Su-Na Wang, Hang Xing, Yi-Zhi Li, Junfeng Bai, Manfred Scheer, Yi Pan and Xiao-Zeng You

Chemical Communications 2007 (Issue 22) pp:2293-2295

Publication Date(Web):07 Mar 2007

DOI:10.1039/B701186E

Two novel chiral metal–organic open frameworks with unprecedented multiwalled tubular channels and interweaving of single-helical and unequal double-helical units were reported, which possess novel four-connected 428310 topology and represent the first examples of functional metal–organic frameworks based on both flexible tripodal and flexible bisdentate ligands.

CuCl-Catalyzed Regio- and Stereoselective Aminohalogenation of α,β-Unsaturated Nitriles

Co-reporter:Jian-Lin Han;Le-Yong Wang;San-Jun Zhi;Guigen Li

European Journal of Organic Chemistry 2007 Volume 2007(Issue 8) pp:1332-1337

Publication Date(Web):17 JAN 2007

DOI:10.1002/ejoc.200600902

α,β-Unsaturated nitriles were found to be suitable substrates for aminochlorination with N,N-dichloro-p-toluenesulfonamide (4-TsNCl₂) in the presence of CuCl as the catalyst (10 mol-%) and 4 Å molecular sieves. The reaction is very convenient to carry out at room temperature without the protection of inert gases, and this method provides an easy route to vicinal haloamino nitriles with excellent regio- and stereoselectivities and in good chemical yields. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Luminescent Open-Framework Antiferromagnet – Hydrothermal Syntheses, Structures, and Luminescent and Magnetic Properties of Two Novel Coordination Polymers: [Zn(pdoa)(bipy)]n and {[Mn(pdoa)(bipy)](bipy)}n [pdoa = 2,2′-(1,3-phenylenedioxy)bis(acetate); bipy = 4,4′-bipyridine]

Co-reporter:Xian-Lan Hong;Junfeng Bai;You Song;Yi-Zhi Li

European Journal of Inorganic Chemistry 2006 Volume 2006(Issue 18) pp:

Publication Date(Web):31 JUL 2006

DOI:10.1002/ejic.200600198

Two coordination polymers of mixed ligands, 2,2′-(1,3-phenylenedioxy)bis(acetate) (pdoa) and 4,4′-bipyridine (bipy),namely [Zn(pdoa)(bipy)]_n (1) and {[Mn(pdoa)(bipy)](bipy)}_n (2), have been hydrothermally synthesized and characterized by single-crystal X-ray diffraction and IR spectra. Complex 1 crystallizes in the triclinic space group P with a = 6.8826(18) Å, b = 11.202(3) Å, c = 12.295(3) Å, α = 86.854(4)°, β = 85.759(5)°, γ = 72.629(4)° and is a novel folded-paper-shaped coordination compound with polymeric sheets formed by the five-coordinate Zn^II centers and bridging pdoa and bipy. Complex 2 crystallizes in the monoclinic space group P2₁/c with a = 11.507(2) Å, b = 23.254(5) Å, c = 9.8710(19) Å, β = 96.418(4)° and exhibits a robust three-dimensional framework with nanosized rectangular channels (11.627 × 11.507 Å). They both display blue fluorescent emission and could be considered as new luminescent materials. In addition, the magnetic properties of complex 2 were investigated and the magnetic susceptibility data were rationally fitted with g = 2.072(5), J = –1.11(4) cm^–1, and zJ′ =–0.161(7) cm^–1, showing it is an unprecedented luminescent open-framework antiferromagnet.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Synthesis and asymmetric catalytic activities of chiral organogallium and indium complexes with ephedrine derivatives as ligands. The crystal structure of [(1R, 2S)-(Me2Ga-μ-OCH(C6H5)CH(CH3)-μ-NHCH3)]2

Co-reporter:Fang Yuan, Chengjian Zhu, Jiangtao Sun, Yongjiang Liu, Yi Pan

Journal of Organometallic Chemistry 2003 Volume 682(1–2) pp:102-107

Publication Date(Web):1 October 2003

DOI:10.1016/S0022-328X(03)00710-1

Reactions of trimethylgallium or trimethylindium with (1R, 2S)-(−)-ephedrine derivatives afford compounds [(1R, 2S)-(Me2E-μ-OCH(C6H5)CH(CH3)-μ-NRCH3)]2 [E=Ga, R=H (1), CH3 (2), CH2Ph (3); E=In, R=H (4), CH3 (5), CH2Ph (6)] in high yields. The resulting complexes 1–6 have been characterized by 1H-NMR spectroscopy and elemental analysis. Structure of the compound 1 determined by single-crystal X-ray analysis shows a dimeric feature containing a standard parallelogram Ga2O2 core bridging through the oxygen atom of ephedrine group. The catalytic asymmetric isocyanosilylation of meso cyclohexene oxide with trimethylsilyl cyanide has been realized with complexes 1–6 as catalysts.Reactions of trimethylgallium or trimethylindium with (1R, 2S)-(−)-ephedrine derivatives afford chiral compounds [(1R, 2S)-(Me2E-μ-OCH(C6H5)CH(CH3)-μ-NRCH3)]2 [E=Ga, R=H (1), CH3 (2), CH2Ph (3); E=In, R=H (4), CH3 (5), CH2Ph (6)] in high yields. Structure of the compound 1 determined by single-crystal X-ray analysis shows a dimeric feature containing a standard parallelogram Ga2O2 core bridging through the oxygen atom of ephedrine group. The catalytic asymmetric isocyanosilylation of cyclohexene oxide with trimethylsilyl cyanide has been examined with complexes 1–6 as catalysts.

Unprecedented interweaving of single-helical and unequal double-helical chains into chiral metal–organic open frameworks with multiwalled tubular structures

Co-reporter:Su-Na Wang, Hang Xing, Yi-Zhi Li, Junfeng Bai, Manfred Scheer, Yi Pan and Xiao-Zeng You

Chemical Communications 2007(Issue 22) pp:NaN2295-2295

Publication Date(Web):2007/03/07

DOI:10.1039/B701186E

Asymmetric synthesis of (3S,1′S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

Co-reporter:Ping Qian, Chen Xie, Lingmin Wu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 40) pp:NaN7913-7913

Publication Date(Web):2014/09/02

DOI:10.1039/C4OB01453G

Asymmetric Mannich reactions of imidazo[2,1-b]thiazole-derived nucleophiles with (SS)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine

Co-reporter:Haibo Mei, Chen Xie, Lingmin Wu, Vadim A. Soloshonok, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 46) pp:NaN8021-8021

Publication Date(Web):2013/10/17

DOI:10.1039/C3OB41785A

Ligand-free palladium-catalyzed intramolecular Heck reaction of secondary benzylic bromides

Co-reporter:Wei Zhou, Guanghui An, Guangqian Zhang, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 16) pp:NaN5837-5837

Publication Date(Web):2011/05/27

DOI:10.1039/C1OB05231D

N,N-Diisopropyl-N-phosphonyl imines lead to efficient asymmetric synthesis of aziridine-2-carboxylic esters

Co-reporter:Padmanabha V. Kattamuri, Yiwen Xiong, Yi Pan and Guigen Li

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 20) pp:NaN3408-3408

Publication Date(Web):2013/03/19

DOI:10.1039/C3OB40251G

Copper-catalyzed aminobromination/elimination process: an efficient access to α,β-unsaturated vicinal haloamino ketones and esters

Co-reporter:Hao Sun, Guangqian Zhang, Sanjun Zhi, Jianlin Han, Guigen Li and Yi Pan

Organic & Biomolecular Chemistry 2010 - vol. 8(Issue 19) pp:NaN4239-4239

Publication Date(Web):2010/08/13

DOI:10.1039/C0OB00283F

A facile process for the asymmetric synthesis of β-trifluoromethylated β-amino ketonesvia addition of ketone enolates to sulfinylimine

Co-reporter:Haibo Mei, Yiwen Xiong, Jianlin Han and Yi Pan

Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 5) pp:NaN1406-1406

Publication Date(Web):2011/01/05

DOI:10.1039/C0OB00586J

New catalytic system for aminohalogenation of β-methyl-β-nitrostyrenes to give opposite regiochemistry

Co-reporter:San-Jun Zhi, Hao Sun, Guangqian Zhang, Guigen Li and Yi Pan

Organic & Biomolecular Chemistry 2010 - vol. 8(Issue 3) pp:NaN631-631

Publication Date(Web):2009/12/07

DOI:10.1039/B914944A

Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

Co-reporter:Parminder Kaur, Gaurav Shakya, Hao Sun, Yi Pan and Guigen Li

Organic & Biomolecular Chemistry 2010 - vol. 8(Issue 5) pp:NaN1096-1096

Publication Date(Web):2010/01/05

DOI:10.1039/B923914F

CAS:225-51-4

Benz[c]acridine

1-chloro-3-[(Z)-(3-chlorophenyl)-NNO-azoxy]benzene

CAS:139-24-2

1-chloro-3-[(Z)-(3-chlorophenyl)-NNO-azoxy]benzene

CAS:118-34-3

Eleutheroside B

CAS:107-89-1

3-hydroxybutyraldehyde

CAS:93-07-2

3,4-Dimethoxybenzoic acid

CAS:74-86-2

ACETYLENE

CAS:1415089-19-8

N-[3-(TRIDECYLOXY)PROPYL]-1,3-PROPANEDIAMINE

CAS:1247348-77-1

N-[3-(TRIDECYLOXY)PROPYL]-1,3-PROPANEDIAMINE

1H-Indole-2,3-dione, 6-chloro-1-(phenylmethyl)-

CAS:1017609-56-1

1H-Indole-2,3-dione, 6-chloro-1-(phenylmethyl)-

Cyclohexanone, 2-[(R)-hydroxy[4-(trifluoromethyl)phenyl]methyl]-, (2S)-

CAS:898542-87-5

Cyclohexanone, 2-[(R)-hydroxy[4-(trifluoromethyl)phenyl]methyl]-, (2S)-