Selective trifluoromethylthiolation of heteroaromatic sp2 C-H bonds with the 2nd generation of trifluoromethanesulfenamide reagent

被引：36

作者：

Alazet, Sebastien ^{[1
,2
]}

Zimmer, Luc ^{[2
,3
]}

Billard, Thierry ^{[1
,2
]}

机构：

[1] Univ Lyon 1, CNRS, ICBMS UMR CNRS 5246, Inst Chem & Biochem, F-69622 Lyon, France

[2] Grp Hosp Est, CERMEP In Vivo Imaging, F-69003 Lyon, France

[3] Grp Hosp Est, UMR CNRS 5292, UMR INSERM 1028, Lyon Neurosci Res Ctr, F-69003 Lyon, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2015年 / 171卷

关键词：

Trifluoromethylthiolation; Trifluoromethanesulfenamide; Heteroarenes; Selective deprotonation; Heteroaromatic; COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION; ARYL BORONIC ACIDS; FLUORINE;

D O I：

10.1016/j.jfluchem.2014.09.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By applying a well-established protocol of selective deprotonation of heteroarenes, the selective trifluoromethylthiolation of various heteroaromatic compounds has been performed, by using the 2nd generation of trifluoromethanesulfenamide reagent. With such strategy, functionalized heteroarenes could be synthesized as potential trifluoromethylthiolated building-blocks. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：78 / 81

页数：4

共 37 条

[1] Electrophilic Trifluoromethylthiolation of Carbonyl Compounds [J].

Alazet, Sebastien ;

Zimmer, Luc ;

Billard, Thierry .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) :8589-8593

[2] Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide [J].

Alazet, Sebastien ;

Ollivier, Kevin ;

Billard, Thierry .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :2354-2357

[3] Base-Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes [J].

Alazet, Sebastien ;

Zimmer, Luc ;

Billard, Thierry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) :10814-10817

[4]

[Anonymous], 2010, Handbook of Heterocyclic Chemistry

[5]

[Anonymous], 2012, Absorptionand Drug Development, DOI [DOI 10.1002/9781118286067.CH8, 10.1002/9781118286067.ch8]

[6]

[Anonymous], 2013, MODERN FLUOROORGANIC

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

Baert, Francois ;

Colomb, Julie ;

Billard, Thierry .

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

[8]

Becker A., 1996, Inventory of Industrial Fluoro-Biochemicals

[9]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895

[10] Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation [J].

Boiko, Vladimir N. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6 :880-921

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