Regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of perfluoroarenes with aryl thioacetates or benzyl thioacetate

Practical and straightforward method for regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of electron-deficient perfluoroarenes with aryl thioacetates or benzyl thioacetate has been developed. Because of its high reaction efficiency, good chemoselect...

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Bibliographic Details
Published inTetrahedron Vol. 68; no. 22; pp. 4233 - 4241
Main Authors Zhou, Qizhong, Zhang, Bin, Du, Tieqi, Gu, Haining, Jiang, Huajiang, Chen, Rener
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.06.2012
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
HALIDES
ACTIVATION
DIRECT ARYLATION
ELECTRON-DEFICIENT POLYFLUOROARENES
THIOLATE ANION
ARENES
NUCLEOPHILE
H BONDS
DERIVATIVES
ALKENYLATION
Drug
Catalytic reaction
Regioselectivity
Chemoselectivity
Transition metal
Chemical substitution
Organic sulfide
Copper ion
Benzylic compound
Aromatic compound
Fluorine Organic compounds
Copper
Functional group
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Summary:Practical and straightforward method for regioselective C–S bond formation accomplished by copper-catalyzed regioselective C–F substitution of electron-deficient perfluoroarenes with aryl thioacetates or benzyl thioacetate has been developed. Because of its high reaction efficiency, good chemoselectivity and regioselectivity, and excellent functional-group compatibility, this protocol provides a useful and operationally simple access to polyfluoroaryl thioethers used for drugs and material chemistry. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.03.091