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A Pd(II)-catalyzed regioselective dual C(sp3)–H/C7(sp2)–H activation and annulation of 8-methylquinoline N-oxides with maleimide has been accomplished[1]. The use of N-oxide as a weak directing group under Pd(II)-complex catalysis activates the initial C(sp3)–H and triggers a relayed, second C7(sp2)–H activation. The dual C–H bond activation, [3 + 2]-annulation, facile introduction and removal of the directing group, substrate scope, and functional group diversity are the important practical features.

[1] Dual C(sp3)–H and C(sp2)–H Activation of 8-Methylquinoline N-Oxides: A Route to Access C7–H Bond. DOI:10.1021/acs.orglett.4c02584