1. Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis
- Author
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LI, YanJie, Li, Yanjie, Miyazawa, Kazuki, Koike, Takashi, and AKITA, MUNETAKA
- Subjects
Reaction conditions ,chemistry.chemical_classification ,chemistry.chemical_compound ,chemistry ,Aryl ,Radical ,Organic Chemistry ,Visible light irradiation ,Pyridine ,Photocatalysis ,Photoredox catalysis ,Photochemistry ,Alkyl - Abstract
A facile and environmentally benign protocol for alkyl- and aryl-thioalkylation of olefins has been developed. Photoredox catalysis with an Ir photocatalyst, [Ir(dF(CF3)ppy)2(bpy)](PF6) (dF(CF3)ppy: 5-trifluoromethyl-2-(2,4-difluorophenyl)pyridine, bpy: 2,2′-bipyridine), induces efficient oxidation of a variety of alkyl- and aryl-thioalkyltrifluoroborates under visible light irradiation at room temperature, leading to the generation of α-thioalkyl radicals via deboronation. The generated α-thioalkyl radicals smoothly react with electron-deficient olefins to afford addition products in good yields. The present photocatalytic method provides us with simple and new access to a range of alkylsulphides under mild reaction conditions.
- Published
- 2015