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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2017
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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. |
format | Online Article Text |
id | pubmed-5390801 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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