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 › peer-review

31 Scopus citations

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
State	Published - 12 Jan 2014

Keywords

Fluorescence
Fusion reactions
Nucleophilic aromatic substitution
Porphyrinoids
Subporphyrins

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10.1002/chem.201405110

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title = "Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin: Synthesis of a thiopyrane-fused subporphyrin",

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.",

keywords = "Fluorescence, Fusion reactions, Nucleophilic aromatic substitution, Porphyrinoids, Subporphyrins",

author = "Daiki Shimizu and Hirotaka Mori and Masaaki Kitano and Cha, \{Won Young\} and Juwon Oh and Takayuki Tanaka and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2014 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2014",

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day = "12",

doi = "10.1002/chem.201405110",

language = "English",

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TY - JOUR

T1 - Nucleophilic aromatic substitution reactions of meso-Bromosubporphyrin

T2 - Synthesis of a thiopyrane-fused subporphyrin

AU - Shimizu, Daiki

AU - Mori, Hirotaka

AU - Kitano, Masaaki

AU - Cha, Won Young

AU - Oh, Juwon

AU - Tanaka, Takayuki

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2014/1/12

Y1 - 2014/1/12

N2 - 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.

AB - 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.

KW - Fluorescence

KW - Fusion reactions

KW - Nucleophilic aromatic substitution

KW - Porphyrinoids

KW - Subporphyrins

UR - https://www.scopus.com/pages/publications/84915748651

U2 - 10.1002/chem.201405110

DO - 10.1002/chem.201405110

M3 - Article

AN - SCOPUS:84915748651

SN - 0947-6539

VL - 20

SP - 16194

EP - 16202

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 49

ER -

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

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