Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

Zhang-Gao Le; Zhen-Chu Chen; Yi Hu; Qinguo Zheng

doi:10.1055/s-2004-829182

Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

Zhang-Gao Le, Zhen-Chu Chen, Yi Hu, Qinguo Zheng

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1951-1954
Number of pages	4
Journal	Synthesis
Volume	2004
Issue number	12
DOIs	https://doi.org/10.1055/s-2004-829182
Publication status	Published - 19 Aug 2004

Keywords

acylation
alkylation
ionic liquids
pyrroles
substitution
sulfonylation

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title = "Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole",

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.",

keywords = "acylation, alkylation, ionic liquids, pyrroles, substitution, sulfonylation",

author = "Zhang-Gao Le and Zhen-Chu Chen and Yi Hu and Qinguo Zheng",

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T1 - Organic reactions in ionic liquids

T2 - A simple and highly regioselective N-substitution of pyrrole

AU - Le, Zhang-Gao

AU - Chen, Zhen-Chu

AU - Hu, Yi

AU - Zheng, Qinguo

PY - 2004/8/19

Y1 - 2004/8/19

N2 - 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.

AB - 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.

KW - acylation

KW - alkylation

KW - ionic liquids

KW - pyrroles

KW - substitution

KW - sulfonylation

UR - http://www.scopus.com/inward/record.url?scp=4444239034&partnerID=8YFLogxK

UR - https://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2004-829182

U2 - 10.1055/s-2004-829182

DO - 10.1055/s-2004-829182

M3 - Article

SN - 0039-7881

VL - 2004

SP - 1951

EP - 1954

JO - Synthesis

JF - Synthesis

IS - 12

ER -

Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

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