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Construction of N-Polyheterocycles by N-Heterocyclic Carbene Catalysis via a Regioselective Intramolecular Radical Addition/Cyclization Cascade.

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N-Polyheterocycles are rapidly accessed by N-heterocyclic carbene (NHC) catalysis through regioselective sequential radical addition/cyclization in the absence of any metals or oxidants. The transformation occurs under mild conditions and enjoys… Click to show full abstract

N-Polyheterocycles are rapidly accessed by N-heterocyclic carbene (NHC) catalysis through regioselective sequential radical addition/cyclization in the absence of any metals or oxidants. The transformation occurs under mild conditions and enjoys a wide substrate scope with excellent functional group compatibility. Furthermore, a gram-scale synthesis is also conducted. Preliminary mechanistic studies reveal the potential involvement of an NHC radical cation intermediate.

Keywords: catalysis; addition cyclization; radical addition; heterocyclic carbene

Journal Title: Organic letters
Year Published: 2022

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