Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis. Issue 4 (27th February 2015)

• Record Type: Journal Article
• Authors: Li, Yanjie; Miyazawa, Kazuki; Koike, Takashi; Akita, Munetaka
• Is Part Of: Organic chemistry frontiers. Volume 2:Issue 4(2015:Apr.)
• Page Start: 319
• Page End: 323
• Publication Date: 2015-02-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c4qo00352g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A new photocatalytic alkyl- and aryl-thioalkylation of electron-deficient olefins using organotrifluoroborates has been developed. 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.