Issue 41, 2019

Deoxygenative trifluoromethylthiolation of carboxylic acids


Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an “umpolung” strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation.

Graphical abstract: Deoxygenative trifluoromethylthiolation of carboxylic acids

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Article information

Article type
Edge Article
09 Jul 2019
26 Aug 2019
First published
26 Aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 9555-9559

Deoxygenative trifluoromethylthiolation of carboxylic acids

R. Mao, S. Bera, A. Cheseaux and X. Hu, Chem. Sci., 2019, 10, 9555 DOI: 10.1039/C9SC03396C

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