On the two-component microwave-mediated reaction of isonitriles with carboxylic acids: regarding alleged formimidate carboxylate mixed anhydrides

J Am Chem Soc. 2008 Oct 8;130(40):13222-4. doi: 10.1021/ja8047078. Epub 2008 Sep 11.

Abstract

Microwave induced two-component coupling (2CC) reaction of carboxylic acids with isonitriles gives rise to various N-formylamides. The formimidate carboxylate mixed anhydride (FCMA) is proposed as the reactive intermediate, which undergoes 1,3-O-->N acyl transfer to give the observed product. The formation and survival of the labile FCMA system has been evaluated.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemistry*
  • Anhydrides / chemistry*
  • Carboxylic Acids / chemistry*
  • Formates / chemistry*
  • Microwaves*
  • Models, Molecular
  • Molecular Structure
  • Nitriles / chemistry*

Substances

  • Amides
  • Anhydrides
  • Carboxylic Acids
  • Formates
  • Nitriles