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Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
53
Issue
35
Identifiers
DOI: 10.1016/j.tetlet.2012.06.135
Keywords
  • Benzamide
  • Superacid
  • Superelectrophile
  • Friedel–Crafts
  • Carboxamidation
Disciplines
  • Chemistry

Abstract

Abstract Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel–Crafts carboxamidation of arenes. The reaction works best in an excess of Brønsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.

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