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

[1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks [J].

Ahrens, Theresia ;

Kohlmann, Johannes ;

Ahrens, Mike ;

Braun, Thomas .

CHEMICAL REVIEWS, 2015, 115 (02) :931-972

[2] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[3] Imidazolylidenes, imidazolinylidenes and imidazolidines [J].

Arduengo, AJ ;

Krafczyk, R ;

Schmutzler, R ;

Craig, HA ;

Goerlich, JR ;

Marshall, WJ ;

Unverzagt, M .

TETRAHEDRON, 1999, 55 (51) :14523-14534

[4] Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid [J].

Bera, Srikrishna ;

Samanta, Ramesh C. ;

Daniliuc, Constantin G. ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9622-9626

[5] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[6] N-Heterocyclic Carbene-Catalyzed Michael Additions of 1,3-Dicarbonyl Compounds [J].

Boddaert, Thomas ;

Coquerel, Yoann ;

Rodriguez, Jean .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (07) :2266-2271

[7] Organocatalytic Activity of N-Heterocyclic Carbenes in the Michael Addition of 1,3-Dicarbonyl Compounds: Application to a Stereoselective Spirocyclization Sequence [J].

Boddaert, Thomas ;

Coquerel, Yoann ;

Rodriguez, Jean .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1744-1748

[8] N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].

Bode, Jeffrey W. ;

Sohn, Stephanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+

[9] N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes [J].

Bugaut, Xavier ;

Liu, Fan ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8130-8133

[10] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

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