Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids

Org Lett. 2011 Nov 18;13(22):6114-7. doi: 10.1021/ol202609a. Epub 2011 Oct 20.

Abstract

The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd(2)(dba)(3) and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Boronic Acids / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Molecular Structure
  • Oxazines / chemistry*
  • Oxygen / chemistry
  • Palladium / chemistry*

Substances

  • Boronic Acids
  • Carboxylic Acids
  • Oxazines
  • Palladium
  • isatoic anhydride
  • Oxygen