Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 9, Pages 4493-4499Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c00123
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Funding
- JSPS KAKENHI [JP17H06442, 18H05969, 19J23073]
- Grants-in-Aid for Scientific Research [19J23073, 18H05969] Funding Source: KAKEN
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We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising a photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from the alpha-C-H bond of an alcohol substrate to the thiyl radical of the photooxidized organocatalyst, interception of the generated carbon-centered radical with a nickel catalyst, and beta-hydride elimination. The reaction proceeded in high yield under mild conditions without producing side products (except H-2 gas) from various alcohols, including sterically hindered alcohols, a steroid, and a pharmaceutical derivative. This catalyst system also promoted acceptorless cross-dehydrogenative esterification from aldehydes and alcohols through hemiacetal intermediates.
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