Facile Pd(II)- and Ni(II)-catalyzed isomerization of terminal alkenes into 2-alkenes

J Org Chem. 2009 Jun 19;74(12):4565-72. doi: 10.1021/jo900180p.

Abstract

Mono- and 2,2'-disubstituted terminal alkenes can be isomerized into the more stable internal (Z)- and (E)-alkenes by treating them with catalytic amounts of [(allyl)PdCl](2) or [(allyl)NiBr](2), a triarylphosphine, and silver triflate at room temperature. The isomeric ratio (E:Z) depends on the alkenes, the E-isomer being the major one. The reaction is tolerant to a wide variety of functional groups including other reactive olefins. Unlike the more reactive Ir catalysts, monosubstituted alkenes give almost exclusively the 2-alkenes. Direct comparison to two of the best-known catalysts for this process {[Ir(PCy(3))(3)](+)[BPh(4)](-) and Grubbs generation II metathesis catalyst} is also described.

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.

MeSH terms

  • Alkenes / chemistry*
  • Allyl Compounds / chemistry
  • Benzene Derivatives / chemistry
  • Bromides / chemistry
  • Chlorides / chemistry
  • Cyclohexenes / chemistry
  • Isoindoles / chemistry
  • Isomerism
  • Nickel
  • Palladium

Substances

  • Alkenes
  • Allyl Compounds
  • Benzene Derivatives
  • Bromides
  • Chlorides
  • Cyclohexenes
  • Isoindoles
  • Palladium
  • Nickel