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Chem Commun (Camb). 2012 Aug 21;48(65):8141-3. doi: 10.1039/c2cc34062c. Epub 2012 Jul 10.

Friedel-Crafts-type reactions with ureas and thioureas.

Chemical communications (Cambridge, England)

Erum K Raja, Sten O Nilsson Lill, Douglas A Klumpp

Affiliations

  1. Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.

PMID: 22777653 DOI: 10.1039/c2cc34062c

Abstract

Despite the relatively low reactivities of urea and thiourea functional groups towards nucleophilic attack, we have found conditions in which they are useful substrates in Friedel-Crafts reactions. The Brønsted superacid, triflic acid, promotes these reactions and a mechanism is proposed involving dicationic, superelectrophilic intermediates.

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