Nucleophilic Aromatic Substitution Reactions of meso-Bromosubporphyrin: Synthesis of a Thiopyrane-Fused Subporphyrin
Nucleophilic Aromatic Substitution Reactions of meso-Bromosubporphyrin: Synthesis of a Thiopyrane-Fused Subporphyrin
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DOI：
10.1002/chem.201405110
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发表时间：
2014-12-01
影响因子：
4.3
通讯作者：
Osuka, Atsuhiro
中科院分区：
文献类型：
--
作者：
Shimizu, Daiki;Mori, Hirotaka;Osuka, Atsuhiro
meso-溴代亚卟啉与芳基胺、二芳基胺、苯酚、乙醇、硫酚和正丁烷乙基化物在合适的碱存在下进行亲核芳族取代（SNAr）反应，得到相应的取代产物。吡咯、吲哚和咔唑的SNAr反应也进行得很好，以中等至良好的产率提供取代产物。最后，与2-溴苯硫酚的SNAr反应和随后的分子内周边芳基化反应提供了一个噻喃稠合亚卟啉。
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.