Enabling Efficient Synthesis of Dihydrostilbenoid via Palladium-Catalyzed Redox-Neutral Deacylative Arylation
Yafei Wan, Tengfei Kang, Zhen Xu, Weikang Xiong, Gang Li, Jianyang Dong, Dong Xue
Abstract
Carbon–Carbon (C–C) bonds constitute the fundamental framework of organic molecules, and their cleavage and reorganization play pivotal roles in both biological systems and industrial processes. Herein, we present a palladium-catalyzed deacylative arylation of diverse methyl ketones under light-free and redox-neutral conditions, offering an efficient approach to constructing C(sp 2 )–C(sp 3 ) bonds. This radical cross-coupling protocol features a broad substrate scope and good functional group compatibility, facilitating the late-stage modification of drug molecules and the synthesis of bioactive natural dihydrostilbenoids. The process leverages a redox-neutral mechanism, wherein the palladium complex serves as an oxidant and the ketone-derived prearomatic intermediates (PAIs) act as a reductant. Mechanistic investigations validate our hypothesis regarding the dual roles of the palladium complex in this transformation.