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

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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
Volume49
Issue number26
DOIs
Publication statusPublished - 2008 Jun 23

Fingerprint

Pyrroles
divinyl benzene
Alkylation
Thiophenes
Lewis Acids
Styrene
Porphyrins
Catalysts
dipyrromethane
1,3-butadiene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Direct alkylation of pyrrole with vinyl substituted aromatics : versatile precursors for the synthesis of porphyrinoid macrocycles. / Hong, Seong Jin; Jeong, Seung Doo; Yoo, Jaeduk; Kim, Jong Seung; Yoon, Juyoung; Lee, Chang Hee.

In: Tetrahedron Letters, Vol. 49, No. 26, 23.06.2008, p. 4138-4141.

Research output: Contribution to journalArticle

Hong, Seong Jin ; Jeong, Seung Doo ; Yoo, Jaeduk ; Kim, Jong Seung ; Yoon, Juyoung ; Lee, Chang Hee. / Direct alkylation of pyrrole with vinyl substituted aromatics : versatile precursors for the synthesis of porphyrinoid macrocycles. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 26. pp. 4138-4141.
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