Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts

In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidatio...

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Detalles Bibliográficos
Autores principales: Ito, Motoki, Ogawa, Chieko, Yamaoka, Nobutaka, Fujioka, Hiromichi, Dohi, Toshifumi, Kita, Yasuyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257409/
https://www.ncbi.nlm.nih.gov/pubmed/20336022
http://dx.doi.org/10.3390/molecules15031918
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author Ito, Motoki
Ogawa, Chieko
Yamaoka, Nobutaka
Fujioka, Hiromichi
Dohi, Toshifumi
Kita, Yasuyuki
author_facet Ito, Motoki
Ogawa, Chieko
Yamaoka, Nobutaka
Fujioka, Hiromichi
Dohi, Toshifumi
Kita, Yasuyuki
author_sort Ito, Motoki
collection PubMed
description In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts.
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spelling pubmed-62574092018-12-04 Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts Ito, Motoki Ogawa, Chieko Yamaoka, Nobutaka Fujioka, Hiromichi Dohi, Toshifumi Kita, Yasuyuki Molecules Article In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts. Molecular Diversity Preservation International 2010-03-17 /pmc/articles/PMC6257409/ /pubmed/20336022 http://dx.doi.org/10.3390/molecules15031918 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Ito, Motoki
Ogawa, Chieko
Yamaoka, Nobutaka
Fujioka, Hiromichi
Dohi, Toshifumi
Kita, Yasuyuki
Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title_full Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title_fullStr Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title_full_unstemmed Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title_short Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
title_sort enhanced reactivity of [hydroxy(tosyloxy)iodo]benzene in fluoroalcohol media. efficient direct synthesis of thienyl(aryl)iodonium salts
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257409/
https://www.ncbi.nlm.nih.gov/pubmed/20336022
http://dx.doi.org/10.3390/molecules15031918
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