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

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

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

46 Scopus citations

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 (Germany)
Issue number	12
DOIs	https://doi.org/10.1055/s-2004-829182
State	Published - 19 Aug 2004
Externally published	Yes

Keywords

Acylation
Alkylation
Ionic liquids
Pyrroles
Substitution
Sulfonylation

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10.1055/s-2004-829182

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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 = "Le, {Zhang Gao} and Chen, {Zhen Chu} and Yi Hu and Zheng, {Qin Guo}",

year = "2004",

month = aug,

day = "19",

doi = "10.1055/s-2004-829182",

language = "英语",

pages = "1951--1954",

journal = "Synthesis (Germany)",

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publisher = "Georg Thieme Verlag",

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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, Qin Guo

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

U2 - 10.1055/s-2004-829182

DO - 10.1055/s-2004-829182

M3 - 文章

AN - SCOPUS:4444239034

SN - 0039-7881

SP - 1951

EP - 1954

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 12

ER -

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

Abstract

Keywords

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