Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; a catalytic approach to ketenes

Chemistry. 2013 Sep 23;19(39):12953-8. doi: 10.1002/chem.201301731. Epub 2013 Sep 3.

Abstract

One-pot radicals: Cobalt(III)-carbene radicals, generated by metallo-radical activation of diazo compounds and N-tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one-pot tandem transformations to produce differently substituted amides, esters and β-lactams in good isolated yields.

Keywords: carbenes; carbonylation; cobalt; ketenes; porphyrinoids; radicals.

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

  • Amines / chemistry
  • Azo Compounds / chemistry*
  • Catalysis
  • Cobalt / chemistry*
  • Esters
  • Ethylenes / chemistry*
  • Imines / chemistry
  • Ketones / chemistry*
  • Metalloporphyrins / chemical synthesis
  • Metalloporphyrins / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Porphyrins / chemical synthesis
  • Porphyrins / chemistry*
  • beta-Lactams / chemistry

Substances

  • Amines
  • Azo Compounds
  • Esters
  • Ethylenes
  • Imines
  • Ketones
  • Metalloporphyrins
  • Porphyrins
  • beta-Lactams
  • carbene
  • Cobalt
  • ketene
  • Methane