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Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation

Photoredox chemical reactions induced by visible light have undergone a renaissance in recent years. Polypyridyl dyes such as Ir(ppy)(3) and Ru(bpy)(3) are key catalysts in this event, and blue‐ or white‐light irradiation is required for the chemical transformations. However, it remains a challenge...

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Autores principales: Matsuzaki, Kohei, Hiromura, Tomoya, Tokunaga, Etsuko, Shibata, Norio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5390801/
https://www.ncbi.nlm.nih.gov/pubmed/28413756
http://dx.doi.org/10.1002/open.201600172
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author Matsuzaki, Kohei
Hiromura, Tomoya
Tokunaga, Etsuko
Shibata, Norio
author_facet Matsuzaki, Kohei
Hiromura, Tomoya
Tokunaga, Etsuko
Shibata, Norio
author_sort Matsuzaki, Kohei
collection PubMed
description Photoredox chemical reactions induced by visible light have undergone a renaissance in recent years. Polypyridyl dyes such as Ir(ppy)(3) and Ru(bpy)(3) are key catalysts in this event, and blue‐ or white‐light irradiation is required for the chemical transformations. However, it remains a challenge to achieve reactions under the lower energy of red light. We disclose, herein, that trifluoroethoxy‐coated subphthalocyanine realizes the red‐light‐driven trifluoromethylation of alkenes and alkynes with trifluoromethyl iodide in good‐to‐high yields. Perfluoroalkylations were also achieved under red light. The reaction mechanism is discussed with the support of UV/Vis spectroscopy and cyclic voltammetry of trifluoroethoxy‐coated subphthalocyanine. Light irradiation/dark study also supports the proposed mechanism.
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spelling pubmed-53908012017-04-14 Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation Matsuzaki, Kohei Hiromura, Tomoya Tokunaga, Etsuko Shibata, Norio ChemistryOpen Communications Photoredox chemical reactions induced by visible light have undergone a renaissance in recent years. Polypyridyl dyes such as Ir(ppy)(3) and Ru(bpy)(3) are key catalysts in this event, and blue‐ or white‐light irradiation is required for the chemical transformations. However, it remains a challenge to achieve reactions under the lower energy of red light. We disclose, herein, that trifluoroethoxy‐coated subphthalocyanine realizes the red‐light‐driven trifluoromethylation of alkenes and alkynes with trifluoromethyl iodide in good‐to‐high yields. Perfluoroalkylations were also achieved under red light. The reaction mechanism is discussed with the support of UV/Vis spectroscopy and cyclic voltammetry of trifluoroethoxy‐coated subphthalocyanine. Light irradiation/dark study also supports the proposed mechanism. John Wiley and Sons Inc. 2017-02-21 /pmc/articles/PMC5390801/ /pubmed/28413756 http://dx.doi.org/10.1002/open.201600172 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Matsuzaki, Kohei
Hiromura, Tomoya
Tokunaga, Etsuko
Shibata, Norio
Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title_full Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title_fullStr Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title_full_unstemmed Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title_short Trifluoroethoxy‐Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low‐Energy Red‐Light Irradiation
title_sort trifluoroethoxy‐coated subphthalocyanine affects trifluoromethylation of alkenes and alkynes even under low‐energy red‐light irradiation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5390801/
https://www.ncbi.nlm.nih.gov/pubmed/28413756
http://dx.doi.org/10.1002/open.201600172
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