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 journalArticle

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 languageEnglish
Pages (from-to)1951-1954
Number of pages4
JournalSynthesis
Volume2004
Issue number12
DOIs
Publication statusPublished - 19 Aug 2004

Fingerprint

Ionic Liquids
Addition reactions
Pyrroles
Ionic liquids
Olefins
Substitution reactions
Atoms
Halogens
Alkenes

Keywords

  • acylation
  • alkylation
  • ionic liquids
  • pyrroles
  • substitution
  • sulfonylation

Cite this

Le, Zhang-Gao ; Chen, Zhen-Chu ; Hu, Yi ; Zheng, Qinguo. / Organic reactions in ionic liquids : A simple and highly regioselective N-substitution of pyrrole. In: Synthesis. 2004 ; Vol. 2004, No. 12. pp. 1951-1954.
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Organic reactions in ionic liquids : A simple and highly regioselective N-substitution of pyrrole. / Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qinguo.

In: Synthesis, Vol. 2004, No. 12, 19.08.2004, p. 1951-1954.

Research output: Contribution to journalArticle

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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

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AU - Zheng, Qinguo

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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

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