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Synthesis 2004(12): 1951-1954
DOI: 10.1055/s-2004-829182
DOI: 10.1055/s-2004-829182
PAPER
© Georg Thieme Verlag Stuttgart · New York
Organic Reactions in Ionic Liquids: A Simple and Highly Regioselective N-Substitution of Pyrrole
Further Information
Received
25 March 2004
Publication Date:
30 July 2004 (online)
Publication History
Publication Date:
30 July 2004 (online)
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Abstract
In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.
Key words
pyrroles - substitution - ionic liquids - alkylation - sulfonylation - acylation
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