Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3?

Organic Chemistry Frontiers Pub Date: 2017-03-30 DOI: 10.1039/C7QO00198C

Abstract

A copper-catalyzed direct oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3 has been developed. This approach provides straightforward and efficient access to a variety of aryl trifluoromethyl sulfides from an easily prepared and stable nucleophilic trifluoromethylthiolation reagent AgSCF3, and readily available nucleophilic aryl boronic acids, thus avoiding the preparation of electrophilic trifluoromethylthiolating reagents in advance. Preliminary mechanistic experiments indicated that AgSCF3 served as both a source of SCF3 and an oxidant.

Graphical abstract: Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3
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