Photocatalytic Functionalization of Alkenes Enabled by Polyfluoroaryl Migration

Author:

Savchenko Artem G.12,Zubkov Mikhail O.1ORCID,Hu Jinbo3,Dilman Alexander D.1ORCID

Affiliation:

1. N. D. Zelinsky Institute of Organic Chemistry 119991 Moscow Leninsky prosp. 47 Russian Federation

2. Department of Chemistry Moscow State University 119991 Moscow Leninskie Gory 1–3 Russian Federation

3. Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 200032 Shanghai 345 Ling-Ling Road China

Abstract

AbstractVisible light‐mediated photocatalytic approach for the radical functionalization of alkenes bearing the fluorinated aryl sulfide fragment is described. The process occurs in the presence of organic photocatalyst using sulfinates as sources of radicals. The key step of the reaction is the intramolecular 1,4‐migration of the polyfluoroaryl group. In the reaction, three new bonds are formed (two C−C and one C−S bond). The decisive role of fluorine atoms in the reaction efficiency was confirmed by DFT calculations.

Funder

Russian Science Foundation

Publisher

Wiley

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