Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Seong Jin Hong, Seung Doo Jeong, Jaeduk Yoo, Jong Seung Kim, Juyoung Yoon, Chang Hee Lee

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5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.

Original languageEnglish
Pages (from-to)4138-4141
Number of pages4
JournalTetrahedron Letters
Issue number26
Publication statusPublished - 2008 Jun 23


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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