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Ni-Catalyzed Oxygen Transfer from N2O onto sp3-Hybridized Carbons

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Ni,  Shengyang
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Le Vaillant,  Franck
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mateos-Calbet,  Ana
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

Ni, S., Le Vaillant, F., Mateos-Calbet, A., Martin, R., & Cornella, J. (2022). Ni-Catalyzed Oxygen Transfer from N2O onto sp3-Hybridized Carbons. Journal of the American Chemical Society, 144(40), 18223-18228. doi:10.1021/jacs.2c06227.


Cite as: https://hdl.handle.net/21.11116/0000-000B-9BAE-3
Abstract
Herein we disclose a catalytic synthesis of cycloalkanols that harnesses the potential of N2O as an oxygen transfer agent onto sp3-hybridized carbons. The protocol is distinguished by its mild conditions and wide substrate scope, thus offering an opportunity to access carbocyclic compounds from simple precursors even in an enantioselective manner. Preliminary mechanistic studies suggest that the oxygen insertion event occurs at an alkylnickel species and that N2O is the O transfer reagent.