An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium

J Am Chem Soc. 2010 Sep 1;132(34):11825-7. doi: 10.1021/ja1052973.

Abstract

Mg in catalytic amounts as the only metal permits the reductive coupling between benzyl halides and pinacolborane. HBpin acts both as an electrophile and as a reducing agent to regenerate an organomagnesium species in situ. An hydride oxidation mechanism is proposed on the basis of DFT calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Boranes / chemical synthesis*
  • Boranes / chemistry*
  • Catalysis
  • Computer Simulation
  • Magnesium / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzene Derivatives
  • Boranes
  • Magnesium