Palladium-catalyzed intramolecular oxidative coupling involving double C(sp(2))-H bonds for the synthesis of annulated biaryl sultams

J Org Chem. 2014 Sep 5;79(17):8010-9. doi: 10.1021/jo5011334. Epub 2014 Aug 22.

Abstract

The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp(2))-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry
  • Catalysis
  • Hydrogen Bonding
  • Naphthalenesulfonates / chemical synthesis*
  • Naphthalenesulfonates / chemistry
  • Oxidative Coupling
  • Palladium / chemistry

Substances

  • Biphenyl Compounds
  • Naphthalenesulfonates
  • Palladium
  • naphthosultone