Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur

被引：289

作者：

Chen, Chao ^{[1
]}

Xie, Yan ^{[1
]}

Chu, Lingling ^{[1
]}

Wang, Ruo-Wen ^{[1
]}

Zhang, Xingang ^{[1
]}

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

机构：

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

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 10期

基金：

中国国家自然科学基金;

关键词：

aryl boronic acids; copper catalysis; oxidative coupling; sulfur; trifluoromethylthiolation; MEDIATED TRIFLUOROMETHYLATION; BOND-FORMATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; SELECTIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; CONVENIENT SYNTHESIS; MEDICINAL CHEMISTRY; FLUORINATED ETHERS; ARYLBORONIC ACIDS; ROOM-TEMPERATURE;

D O I：

10.1002/anie.201108663

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorinated functionality: The copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF 3 and elemental sulfur at room temperature is described for the first time. This reaction provides a concise and efficient method for the synthesis of aryl trifluoromethyl thioethers (ArSCF 3) under mild conditions. Phen=Phenanthroline. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2492 / 2495

页数：4

共 93 条

[1] Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an inorganic iodide
Adams, DJ
Clark, JH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1456 - 1460
[2] Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides
Adams, DJ
Goddard, A
Clark, JH
Macquarrie, DJ
[J]. CHEMICAL COMMUNICATIONS, 2000, (11) : 987 - 988
[3] [Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]
[4] [Anonymous], J ORG CHEM USSR
[5] [Anonymous], 2012, ANGEW CHEM INT EDIT
[6] [Anonymous], ANGEW CHEM
[7] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation
Ball, Nicholas D.
Gary, J. Brannon
Ye, Yingda
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) : 7577 - 7584
[8] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV)
Ball, Nicholas D.
Kampf, Jeff W.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2878 - +
[9] Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides
Billard, T
Roques, N
Langlois, BR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) : 3813 - 3820
[10] A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides
Billard, T
Langlois, BR
[J]. TETRAHEDRON LETTERS, 1996, 37 (38) : 6865 - 6868

← 1 2 3 4 5 6 7 8 9 10 →