Electrochemical Fluorination of Dithiocarbonates Using a Triarylamine Mediator. Issue 11 (1st August 2021)

• Record Type: Journal Article
• Authors: Okuda, Hirokazu; Taniguchi, Kohei; Inagi, Shinsuke; Fuchigami, Toshio
• Is Part Of: Electroanalysis. Volume 33:Issue 11(2021)
• Page Start: 2296
• Page End: 2301
• Publication Date: 2021-08-01
• Subjects: Electrochemical fluorodesulfurization -- Dithiocarbonate -- Triarylamine mediator -- Benzyl fluoride -- Fluoroether; Electrochemical analysis -- Periodicals; Chemistry, Analytical -- Periodicals; Electrochemistry -- Periodicals; 543.4
• DOI: 10.1002/elan.202100070
• Languages: English
• ISSNs: 1040-0397

Abstract

Abstract: Electrochemical oxidation of O ‐(4‐chlorobenzyl ) S ‐methyl dithiocarbonate using tris(2, 4‐dibromophenyl)amine as a redox mediator was studied by cyclic voltammetric measurements. The triarylamine mediated anodic fluorodesulfurization of O ‐(4‐chlorobenzyl) and O ‐(4‐bromobenzyl) S ‐methyl dithiocarbonates provided 4‐chloro‐ and 4‐bromobenzyl fluorides, respectively in moderate yields. On the other hand, similar anodic fluorination of O ‐(2‐phenethyl) S ‐octyl dithiocarbonate and O ‐(4‐bromophenyl) S ‐methyl dithiocarbonate afforded 2‐phenethyl trifluoromethyl ether and difluoro(methylthio)methyl 4‐bromophenyl ether, respectively. Mechanistic aspects are also discussed. Abstract :