Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine

Rajasekhar Reddy Naredla, Douglas A. Klumpp

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11 Scopus citations

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 Bronsted 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.

Original languageEnglish (US)
Pages (from-to)4779-4781
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number35
DOIs
StatePublished - Aug 29 2012

Bibliographical note

Funding Information:
We gratefully acknowledge the support of the NIH- National Institute of General Medical Sciences ( GM085736-01A1 ).

Keywords

  • Benzamide
  • Carboxamidation
  • Friedel-Crafts
  • Superacid
  • Superelectrophile

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