Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles

High Resolution Image Download MS PowerPoint Slide We describe a transition-metal-free photocatalytic synthesis of CF 3 –BCP–oxindoles via radical cascade annulation. This mild and sustainable protocol employs a bench-stable thianthrenium CF 3 –BCP reagent and activated anilides under visible-light irradiation to efficiently assemble complex scaffolds bearing dual (CF 3 and BCP) bioisosteric features. Mechanistic studies reveal that CF 3 –BCP radical generation proceeds through a previously unreported electron donor–acceptor (EDA) complex between 4CzIPN and the thianthrenium salt, initiating a radical chain process. This method provides a practical photochemical platform for the late-stage incorporation of CF 3 –BCP motifs into oxindole frameworks and expands the accessible bioisosteric chemical space for drug discovery.