Robust Photocatalytic Method Using Ethylene-Bridged Flavinium Salts for the Aerobic Oxidation of Unactivated Benzylic Substrates

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43923617" target="_blank" >RIV/60461373:22310/21:43923617 - isvavai.cz</a>
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202100024" target="_blank" >https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202100024</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202100024" target="_blank" >10.1002/adsc.202100024</a>

Result language
angličtina
Original language name
Robust Photocatalytic Method Using Ethylene-Bridged Flavinium Salts for the Aerobic Oxidation of Unactivated Benzylic Substrates
Original language description
7,8-Dimethoxy-3-methyl-1,10-ethylenealloxazinium chloride (1a) was found to be a superior photooxidation catalyst among substituted ethylene-bridged flavinium salts (R=7,8-diMeO, 7,8-OCH2O-, 7,8-diMe, H, 7,8-diCl, 7-CF3 and 8-CF3). Selection was carried out based on structure vs catalytic activity and properties relationship investigations. Flavinium salt 1a proved to be robust enough for practical applications in benzylic oxidations/oxygenations, which was demonstrated using a series of substrates with high oxidation potential, i. e., 1-phenylethanol, ethylbenzene, diphenylmethane and diphenylmethanol derivatives substituted with electron-withdrawing groups (Cl or CF3). The unique capabilities of 1a can be attributed to its high photostability and participation via a relatively long-lived singlet excited state, which was confirmed using spectroscopic studies, electrochemical measurements and TD-DFT calculations. This allows the maximum use of the oxidation power of 1a, which is given by its singlet excited state reduction potential of +2.4 V. 7,8-Dichloro-3-methyl-1,10-ethylenealloxazinium chloride (1 h) can be used as an alternative photocatalyst for even more difficult substrates. (Figure presented.). © 2021 Wiley-VCH GmbH
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
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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