Rhodium-catalyzed direct addition of aryl C-H bonds to nitrosobenzenes at room temperature

Org Lett. 2013 Dec 20;15(24):6302-5. doi: 10.1021/ol403187t. Epub 2013 Nov 25.

Abstract

An unprecedented Rh-catalyzed direct addition of aryl C-H bonds to nitrosobenzenes has been developed under very mild reaction conditions (room temperature). The reaction is highly step-, atom-, and redox-economic and compatible with air and water to N-selectively provide a variety of N-diarylhydroxylamines in good to excellent yields. More importantly, this process may provide a new direction for C-N bond formation through direct C(sp(2))-H functionalization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Hydroxylamines / chemical synthesis*
  • Hydroxylamines / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitroso Compounds / chemistry*
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*
  • Temperature*

Substances

  • Hydroxylamines
  • Nitroso Compounds
  • Organometallic Compounds
  • Rhodium
  • nitrosobenzene