Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation

J Am Chem Soc. 2012 Jun 6;134(22):9110-3. doi: 10.1021/ja303527m. Epub 2012 May 24.

Abstract

We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N(2) as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Azides / chemistry*
  • Calixarenes / chemistry*
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*

Substances

  • Amides
  • Azides
  • Organometallic Compounds
  • Calixarenes
  • Rhodium