Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

Org Lett. 2017 Aug 4;19(15):4142-4145. doi: 10.1021/acs.orglett.7b02024. Epub 2017 Jul 19.

Abstract

This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry*
  • Benzoates / chemistry
  • Biphenyl Compounds / chemical synthesis
  • Boronic Acids / chemical synthesis
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Esters / chemical synthesis
  • Ethers / chemical synthesis
  • Naphthalenes / chemical synthesis
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Amines
  • Benzene Derivatives
  • Benzoates
  • Biphenyl Compounds
  • Boronic Acids
  • Carboxylic Acids
  • Coordination Complexes
  • Esters
  • Ethers
  • Naphthalenes
  • Palladium
  • benzoyl chloride