Organic Reactions in Ionic Liquids: A Simple and Highly Regioselective N-Substitution of Pyrrole

Zhang-Gao Lea, Zhen-Chu Chen*, Yi Hu, Qin-Guo Zheng

*Department of Chemistry, Zhejiang University (xi xi campus), Hangzhou, 310028, P. R. China, Email: zhenchucmail.hz.zj.cn

Z.-G. Lea, Z.-C. Chen, Y. Hu, Q.-G. Zheng Synthesis, 2004, 1951-1954.

DOI: 10.1055/s-2004-829182

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Abstract

In ionic liquids [Bmim][PF₆] or [Bmim][BF₄], a highly regioselective N-substitution of pyrrole with alkyl halides, sulfonyl chlorides, and benzoyl chloride gave substituted pyrroles in excellent yields. Michael addition of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford N-alkylpyrroles.

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Organic Reactions in Ionic liquids: N-Alkylation of Phthalimide and Several Nitrogen Heterocycles

Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004, 208-212.

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Key Words

pyrroles, substitution, ionic liquids, alkylation, sulfonylation, acylation, Michael Addition

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ID: J66-Y2004-2260