Photocatalytic Perfluoroalkylation of Disulfides and Diselenides. Syntheses of Perfluoroalkyl Thio- and Seleno-ethers

Abstract

The synthesis of alkyl(aryl)-fluoroalkyl sulfanyl [R(Ar)-S-RF] and aryl- 6 fluoroalkyl selenolyl (Ar-Se-RF) ethers through visible-light photocatalysis has been 7 successfully carried out. This process involves disulfides, and diselenides [R(Ar)-X-X- 8 R(Ar), where X = S or Se], and fluoroalkyl iodides (RF-I) in the presence of a base as an 9 additive under photocatalysis. The photocatalyst Eosin Y and green light-emitting diodes are utilized for irradiation of R(Ar)-S-RF and Ar-Se-RF syntheses. Our method integrates low-energy visible-light photocatalysis, commercially available perfluoroalkylatingreagents (RF-I), and easily obtainable disulfides and diselenides as starting materials.Mechanistic studies and a detailed synthetic procedure for (Ar)-S-RF on a large scale are presented.