Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43929083" target="_blank" >RIV/60461373:22310/24:43929083 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/24:43929083
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc00087k" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc00087k</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4gc00087k" target="_blank" >10.1039/d4gc00087k</a>

Result language
angličtina
Original language name
Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent
Original language description
The drawbacks commonly observed in synthetic methods for alcohol oxidation often stem from the utilization of complex, toxic, hazardous, or waste-producing oxidants. When sensitive or complex substrates bearing several functional groups are to be transformed, the selectivity of oxidation becomes another significant challenge. Herein, a chemoselective and operationally simple catalyst-free and additive-free method is presented for the aerial oxidation of 1-phenylpropargyl and 1-phenylallyl alcohols to their corresponding ketones, requiring only a solvent and visible light irradiation. The crucial role of dimethylsulfoxide (DMSO) as the solvent lies in achieving high chemoselectivity. Singlet oxygen, whose formation is photosensitized by the substrate and the product, is captured by DMSO, thereby preventing the undesired over-oxidation that occurs in other solvents. The application of DMSO to protect the substrate against singlet oxygen represents a novel approach that is potentially applicable to other aerobic photocatalytic processes. © 2024 The Royal Society of Chemistry.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GF21-14200K" target="_blank" >GF21-14200K: Tailoring flavins for organic photocatalysis</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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