Palladium-catalyzed decarbonylative trifluoromethylation of acid fluorides

Sinead T. Keaveney, Franziska Schoenebeck*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

82 Citations (Scopus)
83 Downloads (Pure)

Abstract

While acid fluorides can readily be made from widely available or biomass-feedstock-derived carboxylic acids, their use as functional groups in metal-catalyzed cross-coupling reactions is rare. This report presents the first demonstration of Pd-catalyzed decarbonylative functionalization of acid fluorides to yield trifluoromethyl arenes (ArCF3). The strategy relies on a Pd/Xantphos catalytic system and the supply of fluoride for transmetalation through intramolecular redistribution to the the Pd center. This strategy eliminated the need for exogenous and detrimental fluoride additives and allows Xantphos to be used in catalytic trifluoromethylations for the first time. Our experimental and computational mechanistic data support a sequence in which transmetalation by R3SiCF3 occurs prior to decarbonylation.

Original languageEnglish
Pages (from-to)4073-4077
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number15
DOIs
Publication statusPublished - 3 Apr 2018
Externally publishedYes

Bibliographical note

Copyright the Author(s) 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • carboxylic acids
  • catalysis
  • density functional calculations
  • palladium
  • trifluoromethylation

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