Ru(II)-Catalyzed Oxidative Cross-Dehydrogenative Alkenylations of Aromatic Amides and Ketones with Unactivated Olefins

A weak coordination guided Ru(II)-catalyzed oxidative functionalization of arenes with unactivated olefins is developed, offering a wide variety of ortho-alkenylated benzamides, acetophenones, and benzophenone in high yields. The protocol accommodates several bioactive molecules and allows downstream synthetic manipulations leading to a 2,3-benzodiazepine scaffold. The reaction features a reversible metalation step and favors a regioselective beta-hydride elimination event.

Automated summary

A weakly coordinated Ru(II)-catalyzed oxidative functionalization method was developed for the synthesis of ortho-alkenylated benzamides, acetophenones, and benzophenones from unactivated olefins and arenes. The reaction could accommodate various bioactive molecules and enable downstream synthetic manipulations to afford a 2,3-benzodiazepine scaffold. The reaction proceeds via a reversible metalation step and regioselective beta-hydride elimination event.