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

Abstract

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. © 2013 Royal Society of Chemistry.