Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins

J Am Chem Soc. 2005 Oct 19;127(41):14194-5. doi: 10.1021/ja055363j.

Abstract

A nickel-catalyzed method for the three-component coupling of alkenes (ethylene and alpha olefins), aldehydes, and silyl triflates is described, and this process represents the first catalytic method for coupling aldehydes and alkenes to give allylic alcohol derivatives. Conceptually, the alkene functions as a replacement for an alkenylmetal reagent.

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

  • Aldehydes / chemistry*
  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Catalysis
  • Molecular Structure
  • Nickel / chemistry*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organosilicon Compounds / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkenes
  • Organometallic Compounds
  • Organosilicon Compounds
  • Nickel