Chloride Induced S-C bond selective cleavage of disulfides to access unsymmetrical β-fluorodisulfides
Tengfei Niu1, Jiayuan Zhang1, Yunpeng He1
1Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China. niutf@jiangnan.edu.cn.
Abstract:
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.
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