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A new chelation assisted reaction using a removable 8-aminoquinoline bidentate directing group that permits the ruthenium-catalyzed ortho-C–H bond alkylation of aromatic amides with various α,β-unsaturated ketones under straightforward conditions has been developed. This methodology represents the first efficient utilization of enones in the ortho directed ruthenium-catalyzed addition of C–H bonds to C–C double bonds. The reaction offers a broad scope and a high functional group tolerance.

Ruthenium-catalyzed ortho-C–H bond alkylation of aromatic amides with α,β-unsaturated ketones via bidentate-chelation assistance