Direct Conversion of Carboxylic Acids to Alkyl Ketones

Org Lett. 2017 Jul 7;19(13):3612-3615. doi: 10.1021/acs.orglett.7b01588. Epub 2017 Jun 12.

Abstract

An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Ketones
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Carboxylic Acids
  • Ketones