Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources
Niankai Fu1, Gregory S Sauer1, Song Lin1,2
1Department of Chemistry and Chemical Biology, Cornell University , Ithaca, New York 14853, United States.
Abstract:
We report a Mn-catalyzed electrochemical dichlorination of alkenes with MgCl2 as the chlorine source. This method provides operationally simple, sustainable, and efficient access to a variety of vicinally dichlorinated compounds. In particular, alkenes with oxidatively labile functional groups, such as alcohols, aldehydes, sulfides, and amines, were transformed into the desired vicinal dichlorides with high chemoselectivity. Mechanistic data are consistent with metal-mediated Cl atom transfer as the predominant pathway enabling dual C-Cl bond formation and contradict an alternative pathway involving electrochemical evolution of chlorine gas followed by Cl2-mediated electrophilic dichlorination.
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