Palladium-catalyzed α-arylation of benzylic phosphine oxides

Org Lett. 2014 Jan 3;16(1):130-3. doi: 10.1021/ol403124g. Epub 2013 Dec 2.

Abstract

A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)2/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).

Publication types

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

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Hydrocarbons, Brominated / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oxides / chemical synthesis*
  • Oxides / chemistry
  • Palladium / chemistry*
  • Phosphines / chemical synthesis*
  • Phosphines / chemistry

Substances

  • Benzene Derivatives
  • Hydrocarbons, Brominated
  • Organometallic Compounds
  • Oxides
  • Phosphines
  • Palladium
  • phosphine