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

Abstract

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