N-Heterocyclic carbene-catalyzed stereoselective construction of olefinic carbon-sulfur bonds via cross-coupling reaction of gem-difluoroalkenes and thiols

被引：43

作者：

Cong, Zi-Song ^{[1
]}

Li, Yang-Guo ^{[1
]}

Chen, Lei ^{[1
]}

Xing, Fen ^{[1
]}

Du, Guang-Fen ^{[1
,2
]}

Gu, Cheng-Zhi ^{[1
,3
]}

He, Lin ^{[1
,3
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Shihezi 832000, Xinjiang Uygur, Peoples R China

[2] Lab Mat Oriented Chem Engn Xinjiang Uygur Autonom, Shihezi, Peoples R China

[3] Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 18期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; DYNAMIC KINETIC RESOLUTION; INTERMOLECULAR STETTER REACTION; INTRAMOLECULAR BENZOIN REACTION; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITIONS; TRANSESTERIFICATION/ACYLATION REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; GAMMA-BUTYROLACTONES;

D O I：

10.1039/c7ob00599g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel organocatalytic olefinic carbon-sulfur bond forming reaction was developed. Under the catalysis of 10 mol% stable N-heterocyclic carbene, thiols undergo direct nucleophilic substitution reaction with gem-difluoroalkenes to produce alpha-fluorovinyl thioethers in high yields with excellent Z-selectivity. In this process, bases are not necessary.

引用

页码：3863 / 3868

页数：6

共 142 条

[51] N-Heterocyclic carbene-catalyzed formal cross-coupling reaction of α-haloenals with thiols: organocatalytic construction of sp2 carbon-sulfur bonds [J].

He, Lin ;

Guo, Hao ;

Li, Yuan-Zhen ;

Du, Guang-Fen ;

Dai, Bin .

CHEMICAL COMMUNICATIONS, 2014, 50 (28) :3719-3721

[52] N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds [J].

Hirano, Keiichi ;

Biju, Akkattu T. ;

Piel, Isabel ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) :14190-+

[53] Transition-Metal-Free Trifluoromethylthiolation of N-Heteroarenes [J].

Honeker, Roman ;

Ernst, Johannes B. ;

Glorius, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (22) :8047-8051

[54] An overview of N-heterocyclic carbenes [J].

Hopkinson, Matthew N. ;

Richter, Christian ;

Schedler, Michael ;

Glorius, Frank .

NATURE, 2014, 510 (7506) :485-496

[55] Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes [J].

Hostier, Thomas ;

Ferey, Vincent ;

Ricci, Gino ;

Pardo, Domingo Gomez ;

Cossy, Janine .

ORGANIC LETTERS, 2015, 17 (15) :3898-3901

[56] N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles [J].

Hovey, M. Todd ;

Check, Christopher T. ;

Sipher, Alexandra F. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9603-9607

[57] gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors [J].

Hu, Mingyou ;

Ni, Chuanfa ;

Li, Lingchun ;

Han, Yongxin ;

Hu, Jinbo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) :14496-14501

[58] Synthesis of fluorovinyl pyrazolyl (thio)ethers by the reaction of gem-difluoroalkenes with pyrazolin-5-ones (thiones) [J].

Huang, Tao ;

Zhao, Xianghu ;

Ji, Xinfei ;

Wu, Wei ;

Cao, Song .

JOURNAL OF FLUORINE CHEMISTRY, 2016, 182 :61-68

[59] [4+2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes [J].

Huang, Xue-Liang ;

He, Lin ;

Shao, Pan-Lin ;

Ye, Song .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :192-195

[60] A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds [J].

Huang, Xueliang ;

Goddard, Richard ;

Maulide, Nuno .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (47) :8979-8983

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