Exogenous Ligand-Free NiH-Catalyzed Hydroacylation of Aryl Alkenes with Aroyl Fluorides

Org Lett. 2022 Jul 29;24(29):5412-5416. doi: 10.1021/acs.orglett.2c02110. Epub 2022 Jul 15.

Abstract

Acyl fluorides have emerged as efficient acyl group donors, but these attractive reagents have rarely been utilized in transition-metal-catalyzed hydroacylation. Herein we report a nickel hydride-catalyzed hydroacylation of aryl alkenes using aroyl fluorides. The reaction proceeds without recourse to an exogenous ligand under mild conditions. The synthetic utility of the present method is demonstrated by the glovebox-free, gram-scale reaction and the late-stage derivatization of complex molecules containing pharmaceutical frameworks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes*
  • Catalysis
  • Fluorides*
  • Ligands
  • Nickel

Substances

  • Alkenes
  • Ligands
  • Nickel
  • Fluorides