Transition‐Metal‐Free Mild and Regioselective Alkylation of Quinoline N‐Oxides with Benzylboronates

Comprehensive Summary A KO t Bu‐mediated C2‐benzylation of quinoline N ‐oxides with benzylboronates under mild reaction conditions has been developed. The reaction shows broad scope for both of the quinoline N ‐oxides and benzylboronates, especially, secondary and tertiary benzylboronates are also compatible with this reaction. DFT calculations indicate that the reaction is promoted by the nucleophilic addition of KO t Bu to boronate rather than the deprotonation of benzylic C−H bond with KO t Bu.