Anilide formation from thioacids and perfluoroaryl azides

J Org Chem. 2015 May 1;80(9):4392-7. doi: 10.1021/acs.joc.5b00240. Epub 2015 Apr 13.

Abstract

A metal-free method for fast and clean anilide formation from perfluoroaryl azide and thioacid is presented. The reaction proved highly efficient, displaying fast kinetics, high yield, and good chemoselectivity. The transformation was compatible with various solvents and tolerant to a wide variety of functional groups, and it showed high performance in polar protic/aprotic media, including aqueous buffer systems.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anilides / chemical synthesis*
  • Anilides / chemistry
  • Azides / chemistry*
  • Molecular Structure
  • Sulfhydryl Compounds / chemistry*

Substances

  • Anilides
  • Azides
  • Sulfhydryl Compounds
  • thioacetic acid