Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F20%3A43920647" target="_blank" >RIV/60461373:22310/20:43920647 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/20:43920647
Result on the web
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201901628" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201901628</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201901628" target="_blank" >10.1002/ejoc.201901628</a>

Result language
angličtina
Original language name
Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates
Original language description
New flavin-based photocatalytic systems used for chemoselective aerobic visible-light oxidations have been developed by tuning the flavin structure and reaction conditions. 1,3-Dimethyl-7-trifluoromethylalloxazine (2) and 10-butyl-3-methyl-7-trifluoromethylisoalloxazine (3) were shown to mediate the selective oxidation of benzyl alcohols to form aldehydes in the presence of Cs2CO3. Flavin 3 was superior in the oxidation of toluene derivatives to form aldehydes in the presence of trifluoroacetic acid. On the other hand, photooxidations provided by ethylene-bridged quaternary flavinium salt 1 gave the corresponding carboxylic acids. The usefulness of the developed catalytic systems using 1–3 was also demonstrated in the oxidation of secondary benzylic and aliphatic alcohols, and benzylic methylene groups to form the corresponding ketones. The systems have the advantage of a broad substrate scope and metal-free conditions, which distinguish them from the previously reported flavin photooxidation reactions. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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/GA18-15175S" target="_blank" >GA18-15175S: Oxidative photocatalytic systems with flavinium salts for direct C-H functionalizations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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