Rh(III)-Catalyzed Enone Carbonyl/Ketone-Directed Aerobic C-H Olefination of Aromatics with Unactivated Olefins

A Rh(III)-catalyzed weak enone carbonyl/ketone-assisted aerobic oxidative C-H olefination of aromatics with unactivated alkenes has been developed. This protocol involves cross-dehydrogenative Heck-type olefination reaction of various substituted biologically relevant chalcones and aromatic ketones such as acetophenones and chromones with various functionalized unactivated olefins in moderate to good yields. Further, ortho-alkylation of chalcones with norbornene is also demonstrated. A possible reaction mechanism involving weak chelation-assisted C-H activation/insertion/β-hydride elimination was proposed and supported by the deuterium labeling studies.