Electrophilic Trifluoromethylthiolation of Allylsilanes with Trifluoromethanesulfanamide

被引：92

作者：

Liu, Jianbo ^{[1
]}

Chu, Lingling ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 04期

基金：

中国国家自然科学基金;

关键词：

COPPER-CATALYZED TRIFLUOROMETHYLATION; FREE-RADICAL ADDITION; ARYL BORONIC ACIDS; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; CONVENIENT SYNTHESIS; FLUORINATED ETHERS; TERMINAL ALKENES; SULFIDES; DISULFIDES; THIOETHERS;

D O I：

10.1021/ol400032g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A CH3COCl-promoted allylic trifluoromethylthiolation of allylsilanes with trifluoromethanesulfanamide has been described. The method allows for an efficient synthesis of a wide range of allylic trifluoromethylthiolated compounds under mild conditions.

引用

页码：894 / 897

页数：4

共 48 条

[1] Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an inorganic iodide [J].

Adams, DJ ;

Clark, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1456-1460

[2] Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides [J].

Adams, DJ ;

Goddard, A ;

Clark, JH ;

Macquarrie, DJ .

CHEMICAL COMMUNICATIONS, 2000, (11) :987-988

[3] ARYL FLUOROALKYL SULFIDES .2. PREPARATION BY CONDENSATION OF TRIFLUOROMETHANESULFENYL CHLORIDE WITH AROMATIC SYSTEMS [J].

ANDREADES, S ;

SHEPPARD, WA ;

HARRIS, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) :898-&

[4] Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].

Baert, Francois ;

Colomb, Julie ;

Billard, Thierry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385

[5] Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates [J].

Billard, T ;

Large, S ;

Langlois, BR .

TETRAHEDRON LETTERS, 1997, 38 (01) :65-68

[6] Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides [J].

Billard, T ;

Roques, N ;

Langlois, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3813-3820

[7] A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides [J].

Billard, T ;

Langlois, BR .

TETRAHEDRON LETTERS, 1996, 37 (38) :6865-6868

[8] THE REACTION OF TRIFLUOROMETHANESULFENYL CHLORIDE WITH ENAMINES OF BETA-KETO CARBOXYLIC-ACID ANILIDES [J].

BOGDANOWICZSZWED, K ;

KAWALEK, B ;

LIEB, M .

JOURNAL OF FLUORINE CHEMISTRY, 1987, 35 (02) :317-327

[9] Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].

Chen, Chao ;

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457

[10] Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur [J].

Chen, Chao ;

Xie, Yan ;

Chu, Lingling ;

Wang, Ruo-Wen ;

Zhang, Xingang ;

Qing, Feng-Ling .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) :2492-2495

← 1 2 3 4 5 →