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      Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds

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          Abstract

          This works introduces hypervalent bis-catecholato silicon compounds as versatile sources of alkyl radicals upon visible-light photocatalysis. Using Ir[(dF(CF3)ppy)2(bpy)](PF6) (dF(CF3)ppy = 2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy = bipyridine) as catalytic photooxidant, a series of alkyl radicals, including highly reactive primary ones can be generated and engaged in various intermolecular homolytic reactions. Based on cyclic voltammetry, Stern-Volmer studies, and supported by calculations, a mechanism involving a single-electron transfer from the silicate to the photoactivated iridium complex has been proposed. This oxidative photocatalyzed process can be efficiently merged with nickel-catalyzed Csp2-Csp3 cross-coupling reactions.

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          Most cited references 51

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          Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

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            Visible light photoredox catalysis: applications in organic synthesis.

            The use of visible light sensitization as a means to initiate organic reactions is attractive due to the lack of visible light absorbance by organic compounds, reducing side reactions often associated with photochemical reactions conducted with high energy UV light. This tutorial review provides a historical overview of visible light photoredox catalysis in organic synthesis along with recent examples which underscore its vast potential to initiate organic transformations.
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              Visible-Light Photoredox Catalysis

              In the last few years, visible-light initiated organic transformations have attracted increasing attention. The development of visible-light-promoted photocatalytic reactions, which enable rapid and efficient synthesis of fine chemicals, is highly desirable from the viewpoint of cost, safety, availability, and environmental friendliness. In this Minireview, recent advances made in this fast developing area of research are discussed.
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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley
                14337851
                September 21 2015
                September 21 2015
                July 24 2015
                : 54
                : 39
                : 11414-11418
                Article
                10.1002/anie.201504963
                26216069
                © 2015

                http://doi.wiley.com/10.1002/tdm_license_1.1

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