Suzuki coupling of potassium cyclopropyl- and alkoxymethyltrifluoroborates with benzyl chlorides

J Org Chem. 2012 Mar 16;77(6):2966-70. doi: 10.1021/jo202686p. Epub 2012 Mar 6.

Abstract

Efficient Csp(3)-Csp(3) Suzuki couplings have been developed with both potassium cyclopropyl- and alkoxymethyltrifluoroborates. Moderate to good yields have been achieved in the cross-coupling of potassium cyclopropyltrifluoroborate with benzyl chlorides possessing electron-donating or electron-withdrawing substituents. Benzyl chloride was also successfully cross-coupled to potassium alkoxymethyltrifluoroborates derived from primary, secondary, and tertiary alcohols.

Publication types

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

MeSH terms

  • Benzyl Compounds / chemistry*
  • Borates / chemistry*
  • Cross-Linking Reagents / chemistry*
  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Potassium / chemistry*
  • tert-Butyl Alcohol / analogs & derivatives*
  • tert-Butyl Alcohol / chemistry*

Substances

  • Benzyl Compounds
  • Borates
  • Cross-Linking Reagents
  • Cyclopropanes
  • benzyl chloride
  • tert-Butyl Alcohol
  • Potassium