Selective synthesis of β-alkylpyrroles

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Abstract

β-Alkylpyrroles are key structural motifs found in many natural products and biologically active compounds as well as functional organic materials. For this reason, synthetic chemists continue to be interested in construction of the framework of β-alkylpyrroles. Due to sufficient aromaticity and π-excessive nature of pyrroles, a straightforward approach to β-alkylpyrroles should be electrophilic aromatic substitution (S EAr) toward the pyrrole ring. However, since a primary nucleophilic site of pyrroles is an α-position, some "trick" is required to direct incoming alkyl electrophiles toward a β-position. This Concept article focuses on presenting previous efforts that have been devoted to the synthesis of β-alkylpyrroles, mainly through the SEAr route.

Original languageEnglish
Pages (from-to)4064-4075
Number of pages12
JournalChemistry - A European Journal
Volume17
Issue number15
DOIs
Publication statusPublished - 4 Apr 2011

Keywords

  • alkylation
  • electrophilic aromatic substitution
  • heterocycles
  • pyrroles
  • regioselectivity

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