Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers

We report herein the development of palladium-catalyzed deacylative deuteration of arylketone oxime ethers. This protocol features excellent functional group tolerance, heterocyclic compatibility, and high deuterium incorporation levels. Regioselective deuteration of some biologically important drugs and natural products are showcased via Friedel-Crafts acylation and subsequent deacylative deuteration. Vicinal meta-C-H bond functionalization (including fluorination, arylation, and alkylation) and para-C-H bond deuteration of electro-rich arenes are realized by using the ketone as both directing group and leaving group, which is distinct from aryl halide in conventional dehalogenative deuteration. A palladium-catalyzed deuteration of arylketone oxime ethers has been realized. Regioselective deuteration of some biologically important drugs and natural products is showcased via Friedel-Crafts acylation and subsequent deacylative deuteration. Vicinal difunctionalization of electro-rich arenes is achieved by using the ketone as both directing group and leaving group.+ image