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

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

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 simp...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 144; no. 40; pp. 18223 - 18228
Main Authors: Ni, Shengyang, Vaillant, Franck Le, Mateos-Calbet, Ana, Martin, Ruben, Cornella, Josep
Format: Journal Article
Language:English
Published: American Chemical Society 26-09-2022
Subjects:
Communication
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c06227