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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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Detalles Bibliográficos
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
Descripción
Sumario: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.