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Deoxygenative trifluoromethylthiolation of carboxylic acids

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Abstract

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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Publication details

The article was received on 09 Jul 2019, accepted on 26 Aug 2019 and first published on 26 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03396C
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Deoxygenative trifluoromethylthiolation of carboxylic acids

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

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