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Issue 65, 2012
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Friedel–Crafts-type reactions with ureas and thioureas

Erum K. Raja,a  Sten O. Nilsson Lillb  and  Douglas A. Klumpp*a 
Author affiliations

* Corresponding authors

a Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, United States
E-mail: dklumpp@niu.edu
Fax: 815-753-4802
Tel: 815-753-1959

b Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden
E-mail: stenil@chem.gu.se
Fax: +46-31-772 3840
Tel: +46-31-772 3840

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.

Graphical abstract: Friedel–Crafts-type reactions with ureas and thioureas

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Publication details

The article was received on 06 Jun 2012, accepted on 20 Jun 2012 and first published on 22 Jun 2012


Article type: Communication
DOI: 10.1039/C2CC34062C
Citation: Chem. Commun., 2012,48, 8141-8143
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    Friedel–Crafts-type reactions with ureas and thioureas

    E. K. Raja, S. O. Nilsson Lill and D. A. Klumpp, Chem. Commun., 2012, 48, 8141
    DOI: 10.1039/C2CC34062C

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