title: Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115.
authors.forename: Rajasekhar Reddy
authors.initials: RR
authors.lastname: Naredla
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
keywords: Friedel-Crafts; benzamide; carboxamidation; superacid; superelectrophile