Amidation of saturated C-H bonds catalyzed by electron-deficient ruthenium and manganese porphyrins. A highly catalytic nitrogen atom transfer process

Org Lett. 2000 Jul 27;2(15):2233-6. doi: 10.1021/ol000107r.

Abstract

Amidation of a variety of hydrocarbons with PhI=NTs catalyzed by ruthenium and manganese meso-tetrakis(pentafluorophenyl)porphyrins 1 and 2 afforded N-substituted amides in up to 92% yields with good to excellent substrate conversions. By employing catalyst 2, exceptionally high turnovers (up to 2600) were achieved, and the amidations can be effected by directly using PhI(OAc)(2)/NH(2)R as amidating reagents; in the case of R = COCF(3) a direct amination was realized in up to 90% yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / metabolism*
  • Catalysis
  • Electrons
  • Manganese / metabolism*
  • Metalloporphyrins / chemistry*
  • Metalloporphyrins / metabolism
  • Nitrogen / metabolism*
  • Ruthenium / metabolism*

Substances

  • Amides
  • Metalloporphyrins
  • Manganese
  • Ruthenium
  • Nitrogen