Oxidative addition of phenyl bromide to Pd(BINAP) vs Pd(BINAP)(amine). Evidence for addition to Pd(BINAP)

Org Lett. 2006 Mar 2;8(5):851-4. doi: 10.1021/ol0528890.

Abstract

The rates of oxidative addition of phenyl bromide to [Pd(BINAP)2] have been measured in the presence and absence of added amine to assess a previous hypothesis that addition to [Pd(BINAP)(amine)] is faster than addition to [Pd(BINAP)]. These data show that addition to the amine complex is not faster than addition to [Pd(BINAP)]. Instead, they are consistent with oxidative addition, even in the presence of amine, to [Pd(BINAP)] as the major pathway. These data underscore the value of studying the stoichiometric reactions of isolated complexes when assessing the mechanism of a catalytic process.

Publication types

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

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / pharmacokinetics
  • Bromides / chemistry*
  • Catalysis
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Naphthalenes / pharmacokinetics
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacokinetics
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Thermodynamics

Substances

  • BINAP, 2-naphthol
  • Benzene Derivatives
  • Bromides
  • Naphthalenes
  • Organometallic Compounds
  • Palladium