Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis

J Am Chem Soc. 2015 Mar 11;137(9):3213-3216. doi: 10.1021/jacs.5b00344. Epub 2015 Feb 27.

Abstract

A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.

Publication types

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

MeSH terms

  • Alcohols / chemistry
  • Alkenes / chemistry*
  • Anions / chemistry
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Esters / chemistry
  • Magnetic Resonance Spectroscopy
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Alkenes
  • Anions
  • Boron Compounds
  • Esters
  • Palladium