Propargylic oxidations catalyzed by dirhodium caprolactamate in water: efficient access to alpha,beta-acetylenic ketones

J Org Chem. 2008 Jun 6;73(11):4317-9. doi: 10.1021/jo800382p. Epub 2008 May 1.

Abstract

Dirhodium(II) caprolactamate (1, Rh 2(cap) 4) with 70% w/w aqueous tert-butyl hydroperoxide (T-HYDRO ) is a highly effective catalytic oxidation protocol for the selective C-H oxidation of alkynes to propargylic ketones. The oxidation occurs readily in aqueous solvent under mild conditions with an inexpensive and easily handled oxidant. Alpha,beta-acetylenic carbonyl compounds are formed in up to 80% isolated yield.

Publication types

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

MeSH terms

  • Acetylene / chemistry*
  • Caprolactam / analogs & derivatives*
  • Caprolactam / chemistry*
  • Catalysis
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Spectrometry, Mass, Electrospray Ionization
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • Ketones
  • Organometallic Compounds
  • Water
  • Caprolactam
  • Acetylene