Nucleophilic Aromatic Substitution Reactions of meso-Bromosubporphyrin: Synthesis of a Thiopyrane-Fused Subporphyrin

作者:Shimizu Daiki; Mori Hirotaka; Kitano Masaaki; Cha Won Young; Oh Juwon; Tanaka Takayuki; Kim Dongho*; Osuka Atsuhiro
来源:Chemistry - A European Journal, 2014, 20(49): 16194-16202.
DOI:10.1002/chem.201405110

摘要

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.

  • 出版日期2014-12-1