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Amidative β-Scission of Alcohols Enabled by Dual Catalysis of Photoredox Proton-Coupled Electron Transfer and Inner-Sphere Ni-Nitrenoid Transfer

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Title
Amidative β-Scission of Alcohols Enabled by Dual Catalysis of Photoredox Proton-Coupled Electron Transfer and Inner-Sphere Ni-Nitrenoid Transfer
Author(s)
Hyeyun Keum; Harin Ryoo; Dongwook Kim; Sukbok Chang
Publication Date
2023-12
Journal
Journal of the American Chemical Society, v.146, no.1, pp.1001 - 1008
Publisher
American Chemical Society
Abstract
The photoredox/Ni dual catalysis is an appealing strategy to enable unconventional C-heteroatom bond formation. While significant advances have been achieved using this system, intermolecular C(sp3)-N bond formation has been relatively underdeveloped due to the difficulty in C(sp3)-N reductive elimination. Herein, we present a new mechanistic approach that utilizes dioxazolones as the Ni(II)-nitrenoid precursor to capture carbon-centered radicals by merging proton-coupled electron transfer (PCET) with nickel catalysis, thus forming synthetically versatile N-alkyl amides using alcohols. Based on mechanistic investigations, the involvement of (κ2-N,O)Ni(II)-nitrenoid species was proposed to capture photoredox PCET-induced alkyl radicals, thereby playing a pivotal role to enable the C(sp3)-N bond formation. © 2023 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/14612
DOI
10.1021/jacs.3c11813
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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