Nucleophilic aromatic substitution reactions of meso-bromosubporphyrin: synthesis of a thiopyrane-fused subporphyrin

Abstract

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

Keywords: fluorescence; fusion reactions; nucleophilic aromatic substitution; porphyrinoids; subporphyrins.