Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition

J Am Chem Soc. 2019 Feb 6;141(5):1828-1832. doi: 10.1021/jacs.8b13652. Epub 2019 Jan 29.

Abstract

The first intermolecular carbonyl arylations via transfer hydrogenative reductive coupling are described. Using rhodium catalysts modified by tBu2PMe, sodium formate-mediated reductive coupling of aryl iodides with aldehydes occurs in a chemoselective fashion in the presence of protic functional groups and lower halides. This work expands the emerging paradigm of transfer hydrogenative coupling as an alternative to pre-formed carbanions or metallic reductants in C═X addition.

Publication types

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

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Catalysis
  • Formates / chemistry*
  • Hydrogenation
  • Molecular Structure
  • Reducing Agents / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Formates
  • Reducing Agents
  • formic acid
  • Rhodium