Issue 4, 2015

Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis

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.

Graphical abstract: Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
29 Kax 2014
Accepted
09 Nah 2015
First published
11 Nah 2015

Org. Chem. Front., 2015,2, 319-323

Author version available

Alkyl- and aryl-thioalkylation of olefins with organotrifluoroborates by photoredox catalysis

Y. Li, K. Miyazawa, T. Koike and M. Akita, Org. Chem. Front., 2015, 2, 319 DOI: 10.1039/C4QO00352G

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