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Journal Article

Conjugate Aminocyclization Catalyzed by a Bismuthinidene

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Mato,  Mauro
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wang,  Feng
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Mato, M., Wang, F., & Cornella, J. (2024). Conjugate Aminocyclization Catalyzed by a Bismuthinidene. Advanced Synthesis & Catalysis, 366(4), 740-744. doi:10.1002/adsc.202300857.


Cite as: https://hdl.handle.net/21.11116/0000-000D-E3F8-B
Abstract
We disclose how an N,C,N-bismuthinidene is able to promote an intramolecular conjugate amination that affords cyclic carbamates in 91–97% yields. The reaction proceeds at room temperature in short reaction times, requiring a remarkably low loading of a bismuth(I) complex (0.1 mol%) without the need of an additional Brønsted base. Preliminary mechanistic studies suggest that the reaction takes place through a polar pathway involving the conjugate addition of the nucleophilic bismuthinidene, followed by an intramolecular aza-Michael reaction.