Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin: Synthesis of a thiopyrane-fused subporphyrin

Daiki Shimizu, Hirotaka Mori, Masaaki Kitano, Won Young Cha, Juwon Oh, Takayuki Tanaka, Dongho Kim, Atsuhiro Osuka

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meso-Bromosubporphyrin undergoes nucleophilic aromatic substitution (SNAr) reactions with arylamines, diarylamines, phenols, ethanol, thiophenols, and n-butanethiol in the presence of suitable bases to provide the corresponding substitution products. The SNAr reactions also proceed well with pyrrole, indole, and carbazole to provide substitution products in moderate to good yields. Finally, the SNAr reaction with 2-bromothiophenol and subsequent intramolecular peripheral arylation reaction affords a thiopyrane-fused subporphyrin.

Original languageEnglish
Pages (from-to)16194-16202
Number of pages9
JournalChemistry - A European Journal
Issue number49
Publication statusPublished - 2014 Jan 12


All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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