Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin: Synthesis of a thiopyrane-fused subporphyrin

Daiki Shimizu; Hirotaka Mori; Masaaki Kitano; Won Young Cha; Juwon Oh; Takayuki Tanaka; Dongho Kim; Atsuhiro Osuka

doi:10.1002/chem.201405110

Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin: Synthesis of a thiopyrane-fused subporphyrin

Daiki Shimizu, Hirotaka Mori, Masaaki Kitano, Won Young Cha, Juwon Oh, Takayuki Tanaka, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article

24 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	16194-16202
Number of pages	9
Journal	Chemistry - A European Journal
Volume	20
Issue number	49
DOIs	https://doi.org/10.1002/chem.201405110
Publication status	Published - 2014 Jan 12

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All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Cite this

Shimizu, D., Mori, H., Kitano, M., Cha, W. Y., Oh, J., Tanaka, T., Kim, D., & Osuka, A. (2014). Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin: Synthesis of a thiopyrane-fused subporphyrin. Chemistry - A European Journal, 20(49), 16194-16202. https://doi.org/10.1002/chem.201405110

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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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Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin : Synthesis of a thiopyrane-fused subporphyrin. / Shimizu, Daiki; Mori, Hirotaka; Kitano, Masaaki; Cha, Won Young; Oh, Juwon; Tanaka, Takayuki; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 20, No. 49, 12.01.2014, p. 16194-16202.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin

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AU - Shimizu, Daiki

AU - Mori, Hirotaka

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AU - Oh, Juwon

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AU - Kim, Dongho

AU - Osuka, Atsuhiro

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