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

Zhang-Gao Le; Zhen-Chu Chen; Yi Hu; Qin-Guo Zheng

doi:10.1055/s-2004-829182

PAPER

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

Zhang-Gao Le^a,b,c, Zhen-Chu Chen*^a,b, Yi Hu^b, Qin-Guo Zheng^d
^a Ningbo Institute of Technology, Zhejiang University, Ningbo, 315100, P. R. China
^b Department of Chemistry, Zhejiang University (xi xi campus), Hangzhou, 310028, P. R. China
e-Mail: zhenchuc@mail.hz.zj.cn;
^c Department of Applied Chemistry, East China Institute of Technology, Fuzhou, 344000, P. R. China
^d Pharmaceutical Science Reseach Institute, Aston University, Aston Triangle, Birmingham B4 TET, UK

Abstract

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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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References

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