title: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan).
authors.forename: Daiki
authors.initials: D
authors.lastname: Shimizu
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Mori
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kitano
authors.forename: Won-Young
authors.initials: WY
authors.lastname: Cha
authors.forename: Juwon
authors.initials: J
authors.lastname: Oh
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Dongho
authors.initials: D
authors.lastname: Kim
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Osuka
keywords: fluorescence; fusion reactions; nucleophilic aromatic substitution; porphyrinoids; subporphyrins