Electrochemical Fluorination of Dithiocarbonates Using a Triarylamine Mediator

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 dithiocarbonate...

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Bibliographic Details
Published in:Electroanalysis (New York, N.Y.) N.Y.), 2021-11, Vol.33 (11), p.2296-2301
Main Authors: Okuda, Hirokazu, Taniguchi, Kohei, Inagi, Shinsuke, Fuchigami, Toshio
Format: Article
Language:English
Subjects:
Benzyl fluoride
Dithiocarbonate
Electrochemical fluorodesulfurization
Fluoroether
Triarylamine mediator
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Summary: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.
ISSN:1040-0397
1521-4109
DOI:10.1002/elan.202100070