N-oxide as a traceless oxidizing directing group: mild rhodium(III)-catalyzed C-H olefination for the synthesis of ortho-alkenylated tertiary anilines

Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12970-4. doi: 10.1002/anie.201307174. Epub 2013 Nov 12.

Abstract

Double role: A traceless directing group also acts as an internal oxidant in a novel Rh(III) -catalyzed protocol developed for the synthesis of ortho-alkenylated tertiary anilines. A five-membered cyclometalated Rh(III) complex is proposed as a plausible intermediate and confirmed by X-ray crystallographic analysis.

Keywords: CH activation; anilines; directing groups; olefination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry
  • Catalysis
  • Coordination Complexes / chemistry*
  • Molecular Structure
  • Oxidants / chemistry
  • Oxidation-Reduction
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Aniline Compounds
  • Coordination Complexes
  • Oxidants
  • Rhodium