Copper-Promoted Sulfenylation of sp(2) C-H Bonds

An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative beta-C-H bonds and benzylamine derivative gamma-C-H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90-130 degrees C. Application of this methodology...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 44; pp. 18237 - 18240
Main Authors Ly Dieu Tran, Popov, Ilya, Daugulis, Olafs
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 07.11.2012
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FUNCTIONALIZATION
OXIDATION
AMINATION
ARYL BORONIC ACIDS
TRIFLUOROMETHYLTHIOLATION
ALPHA-FLUORINATED ETHERS
C(SP)-H
THIOETHERS
CATALYZED ARYLATION
GENERAL-METHOD
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Summary:An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative beta-C-H bonds and benzylamine derivative gamma-C-H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90-130 degrees C. Application of this methodology to the direct trifluoromethylsulfenylation of C-H bonds was demonstrated.
Bibliography:NIH RePORTER
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3092278