Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates
Identifikátory výsledku
Kód výsledku v 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>
Nalezeny alternativní kódy
RIV/60461373:22810/20:43920647
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates
Popis výsledku v původním jazyce
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
Název v anglickém jazyce
Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates
Popis výsledku anglicky
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
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/GA18-15175S" target="_blank" >GA18-15175S: Oxidativní fotokatalytické systémy s flaviniovými solemi pro přímé C-H funkcionalizace</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2020
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
—
Svazek periodika
2020
Číslo periodika v rámci svazku
10
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
7
Strana od-do
1579-1585
Kód UT WoS článku
000502155200001
EID výsledku v databázi Scopus
2-s2.0-85076442463