95. Transition-Metal-Free Mild and Regioselective Alkylation of Quinoline N-Oxides with Benzylboronates

Niu,Y.;‡ Liu, J.;‡ Wu, Q.; Xie, X.; Li, Z.;* Jiang, Y.-Y.;* Liu, Y.* Chin. J. Chem. 2025, 43, 2285-2290. Download Link

A KOtBu-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 KOtBu to boronate rather than the deprotonation of benzylic C−H bond with KOtBu.