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Synthesis 2008(6): 897-902  
DOI: 10.1055/s-2008-1032182
PAPER
© Georg Thieme Verlag Stuttgart · New York

Nafion®-H Catalyzed Synthesis of Fluorinated Benzimidazolines, Benzothiazolines, Benzoxazolines and Dihydrobenzoxazinones

G. K. Surya Prakash*, Habiba Vaghoo, Chiradeep Panja, Arpad Molnár, Thomas Mathew, George A. Olah*
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA
Fax: +1(213)7406270; e-Mail: gprakash@usc.edu;
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Publication History

Received 16 November 2007
Publication Date:
18 February 2008 (online)

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Abstract

Nafion®-H, a perfluoroalkanesulfonic acid resin, has been found to be a suitable solid acid catalyst with high selectivity and catalytic activity for the one-pot synthesis of fluorinated benzimidazolines, benzothiazolines, benzoxazolines, and dihydrobenz­oxazinones. These Nafion®-H mediated condensation-cyclization reactions were easily achieved under mild conditions in high yields and purity. Introduction of fluorine atoms favors the formation of these five- and six-membered heterocycles and monofluoro-, difluoro­- and trifluoromethylated derivatives can be prepared in high yields using this method.

Key words

heterogeneous catalysis - perfluoroalkanesulfonic acid resin - condensation-cyclization - fluorinated heterocycles - Nafion®-silica nanocomposites