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

[Display omitted] 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 selec...

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Bibliographic Details
Published in:Tetrahedron letters 2022-02, Vol.91, p.153647, Article 153647
Main Authors: Forni, José A., Czyz, Milena L., Lupton, David W., Polyzos, Anastasios
Format: Article
Language:English
Subjects:
Amines
Arylation
C–H activation
Electrosynthesis
Flow chemistry
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153647