Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis?
Organic Chemistry Frontiers Pub Date: 2015-02-11 DOI: 10.1039/C4QO00352G
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.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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