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

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

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
Volume20
Issue number49
DOIs
Publication statusPublished - 2014 Jan 12

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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