The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins
Alberto Luridiana, Daniele Mazzarella, Luca Capaldo, Juan A. Rincón, Pablo García‐Losada, Carlos Mateos, Michael O. Frederick, Manuel Nuño, Wybren Jan Buma, Timothy Noël
Abstract
) bonds. The mild protocol is fast and scalable using flow technology, displays broad functional group tolerance, and is amenable to a wide variety of medicinally relevant moieties. Mechanistic investigations reveal that the ketone catalyst, upon photoexcitation, is responsible for the direct activation of the silicon-based XAT reagent (HAT-mediated XAT) that furnishes the targeted alkyl radical and is ultimately involved in the turnover of the nickel catalytic cycle.
Topics & Concepts
ChemistryElectrophileCatalysisAlkylRadicalSilylationCatalytic cyclePhotochemistryBenzophenoneChemoselectivityPhotocatalysisCombinatorial chemistryPhotoredox catalysisOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques