Isolation of an σ-alkyl iridium hydride complex, formed in the (semi)hydrogenation of an β-enamido ketone

J Org Chem. 2013 Apr 5;78(7):3425-8. doi: 10.1021/jo4001349. Epub 2013 Mar 8.

Abstract

σ-Alkyl iridium hydride complexes are generally postulated as intermediates in iridium-catalyzed hydrogenation. Fast reductive elimination results in the formation of the hydrogenation product. With an β-enamido ketone as unsaturated substrate, such an intermediate could be trapped because the semihydrogenated product coordinates trifold to the iridium, generating a stable 18e(-) complex, which does not eliminate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogenation
  • Iridium / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / isolation & purification*

Substances

  • Ketones
  • Organometallic Compounds
  • Iridium