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Visible-Light-Driven Bisfunctionalization of Unactivated Olefins via the Merger of Proton-Coupled Electron Transfer and Carbene Catalysis

Bei Zhang, Jianqing Qi, Yuhan Liu, Zhipeng Li, Jian Wang

2021Organic Letters63 citationsDOI

Abstract

Herein, we reported an N-heterocyclic carbene (NHC) and photo-co-catalyzed alkylacylation of olefins in the presence of the versatile synthon diazo ester, providing a new idea for transient radical generation with the only byproduct being N2. Particularly, this radical process employs traditional carbene precursor diazo esters as the radical source, which is the first case in NHC catalysis. Compared to the previous pathway that produces radicals with large discard fragments, this merged channel possesses great atom economy.

Topics & Concepts

CarbeneChemistrySynthonDiazoCatalysisRadicalPhotochemistryProtonCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysicsQuantum mechanicsCyclopropane Reaction MechanismsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization Methods