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Synthesis 2008(16): 2631-2635  
DOI: 10.1055/s-2008-1067178
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Promoted Regioselective α-Tricyanoethenylation of N-Methylpyrroles

Vladislav N. Drichkov, Lyubov’ N. Sobenina, Tamara I. Vakul’skaya, Igor’ A. Ushakov, Al’bina I. Mikhaleva, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publication History

Received 11 April 2008
Publication Date:
17 July 2008 (online)

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Abstract

The reaction of N-methylpyrroles with tetracyanoethylene (TCNE) has been studied in various solvents (DMSO, acetone, THF). A highly efficient protocol for the copper(I)-promoted regioselective α-tricyanoethenylation of N-methylpyrroles has been developed.

Key words

N-methylpyrroles - TCNE - tricyanoethenylation - copper(I) bromide - regioselectivity

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