Chloride Induced S-C bond selective cleavage of disulfides to access unsymmetrical β-fluorodisulfides

Selective S-C bond cleavage of disulfides presents a significant challenge due to the fact that S-S bonds are weaker than S-C bonds. In this study, we present a novel chloride-induced Selectfluor radical cation process for converting readily available symmetrical disulfides into unsymmetrical β-fluo...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-10, Vol.6 (87), p.12714-12717
Main Authors: Niu, Tengfei, Zhang, Jiayuan, He, Yunpeng, Hong, Mei, Zhu, Lei, Lan, Yu
Format: Article
Language:English
Subjects:
Bonding strength
Chlorides
Cleavage
Disulfides
Functional groups
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Summary:Selective S-C bond cleavage of disulfides presents a significant challenge due to the fact that S-S bonds are weaker than S-C bonds. In this study, we present a novel chloride-induced Selectfluor radical cation process for converting readily available symmetrical disulfides into unsymmetrical β-fluorodisulfides through selective S-C bond cleavage. Mechanistic investigations and DFT calculations suggest the involvement of a chlorinated disulfide radical, which subsequently reacts with alkenes to form β-fluorodisulfides via the atom transfer radical addition (ATRA) mechanism. Furthermore, this method exhibits broad functional group tolerance, enabling the synthesis of various target products in moderate to good yields. This work describes a novel chloride anion induced radical-triggered S-C bond selective cleavage of disulfides to access unsymmetrical β-fluorodisulfides by disulfidefluorination of alkenes.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc04065a