Room temperature hydroalkylation of electron-deficient olefins: sp3 C-H functionalization via a lewis acid-catalyzed intramolecular redox event

J Am Chem Soc. 2005 Sep 7;127(35):12180-1. doi: 10.1021/ja053337f.

Abstract

A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

Publication types

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

MeSH terms

  • Acids / chemistry*
  • Alkenes / chemistry*
  • Alkylation
  • Carbon / chemistry*
  • Catalysis
  • Electrons
  • Hydrogen / chemistry*
  • Models, Chemical
  • Oxidation-Reduction
  • Temperature

Substances

  • Acids
  • Alkenes
  • Carbon
  • Hydrogen