Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion

Org Lett. 2009 Sep 17;11(18):4248-50. doi: 10.1021/ol901759t.

Abstract

Exposure of aromatic carboxamides 1e-1m, heteroaromatic carboxamides 1n-1p, and alpha,beta-unsaturated carboxamides 1q-1s to 1,1-dimethylallene in the presence of the a cationic iridium complex derived from [Ir(cod)(2)]BAr(F)(4) and rac-BINAP results in direct C-H prenylation to furnish adducts 2e-2m, 2n-2p, and 2q-2s, respectively, in good isolated yields as single isomers.

Publication types

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

MeSH terms

  • Alkadienes / chemistry*
  • Catalysis
  • Hydrocarbons, Aromatic / chemistry
  • Hydrogenation
  • Iridium / chemistry*
  • Molecular Structure
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Prenylation*
  • Stereoisomerism

Substances

  • Alkadienes
  • Hydrocarbons, Aromatic
  • Oxidants
  • Iridium
  • propadiene