Chemoselective Anaerobic Dehydrogenation of Alcohols by Using Visible Light and a Positively Charged Deazaflavin Catalyst Regenerated by Acetonitrile Solvent
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F25%3A00605119" target="_blank" >RIV/61388963:_____/25:00605119 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/25:43931153 RIV/60461373:22810/25:43931153
Result on the web
<a href="https://doi.org/10.1002/cctc.202401795" target="_blank" >https://doi.org/10.1002/cctc.202401795</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cctc.202401795" target="_blank" >10.1002/cctc.202401795</a>
Alternative languages
Result language
angličtina
Original language name
Chemoselective Anaerobic Dehydrogenation of Alcohols by Using Visible Light and a Positively Charged Deazaflavin Catalyst Regenerated by Acetonitrile Solvent
Original language description
Three series of novel deazaflavinum salts differing in their substitutions at positions 5 (R = H, phenyl, or mesityl), 7, and 8 (R = OMe, Me, H, or Cl) were synthesized as potential catalysts of a novel chemoselective visible light-mediated anaerobic oxidation of primary and secondary alcohols to carbonyl compounds. This mild procedure uses acetonitrile as a solvent, which acts simultaneously as a sacrificial electron acceptor (in place of the oxygen usually used in photooxidation reactions), and therefore the reaction does not need any additives. Structure and properties-versus-catalytic activity studies identified 5-mesityl-7,8-dimethoxy-3-methyldeazaflavinium chloride (3a-Cl) as the most potent catalyst. 3a-Cl was effective in non-deuterated acetonitrile (CH3CN), unlike its original 5-phenyl analogue 2a-Cl, which is efficient only in deuterated solvent (CD3CN). This difference arises because the regeneration of the 2a-Cl catalyst is slower in CH3CN than in CD3CN. Our method using the optimized 3a-Cl photocatalyst and CH3CN as a sacrificial oxidant and solvent in one is a useful addition to synthetic organic chemistry. Anaerobic conditions prevent side oxygenation reactions and overoxidations that usually occur in air or oxygen. This property makes this method suitable for dehydrogenations of alcohols that possess additional group(s) sensitive to oxygenation.
Czech name
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Czech description
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Classification
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
Result continuities
Project
<a href="/en/project/GA23-06465S" target="_blank" >GA23-06465S: Merging photochemistry and electrochemistry in flavin-based redox catalysis</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemCatChem
ISSN
1867-3880
e-ISSN
1867-3899
Volume of the periodical
17
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
e202401795
UT code for WoS article
001384365400001
EID of the result in the Scopus database
2-s2.0-86000387895