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

ABSTRACT: 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.

SUBMITTER: Matsuzaki K

PROVIDER: S-EPMC5390801 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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

Matsuzaki Kohei K Hiromura Tomoya T Tokunaga Etsuko E Shibata Norio N

ChemistryOpen 20170221 2

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 alk ...[more]

PMID: 28413756

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