An electrochemical γ-C–H arylation of amines in continuous flow

    • José A.Fornia
    • Milena L.Czyza
    • David W.Luptonb
    • Anastasios Polyzosa,c
    • aSchool of Chemistry, The University of Melbourne, Parkville 3010, Victoria, Australia
    • bSchool of Chemistry, Monash University, Clayton 3800, Victoria, Australia
    • cCSIRO Manufacturing, Research Way, Clayton VIC 3168, Australia

    Reported here is a regioselective C(sp3)–C(sp2) cross coupling reaction between inert γ-C(sp3)–H bonds in aliphatic amines and cyanoarenes under electrochemical conditions in flow. The developed methodology takes advantage of a removable redox active auxiliary, which triggers selective 1,7-hydrogen atom transfer to functionalise an aliphatic C–H bond at the γ-position of an alkyl amine. In this reaction, a cyanoarene radical anion functions as both a selective arylating reagent and a redox active mediator, enabling the controlled one electron reduction of the redox active auxiliary. This strategy offers a new approach towards γ-C(sp3)–H bond functionalisation allowing generation of, amongst others, sterically crowded carbon centres under mild reaction conditions and in the absence of additional catalysts or radical initiators.

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