Nucleophilic Aromatic Substitution Reactions of meso‐Bromosubporphyrin: Synthesis of a Thiopyrane‐Fused Subporphyrin |
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| Authors: | Daiki Shimizu Hirotaka Mori Masaaki Kitano Won‐Young Cha Juwon Oh Dr. Takayuki Tanaka Prof. Dr. Dongho Kim Prof. Dr. Atsuhiro Osuka |
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| Affiliation: | 1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo‐ku, Kyoto 606‐8502 (Japan);2. Spectroscopy Laboratory for Functional π‐Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120‐749 (Korea) |
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| 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. |
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| Keywords: | fluorescence fusion reactions nucleophilic aromatic substitution porphyrinoids subporphyrins |
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