Flavin Photocatalysts for visible Light [2+2] Cycloadditions: Structure, Reactivity and Reaction Mechanism
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43917088" target="_blank" >RIV/60461373:22310/18:43917088 - isvavai.cz</a>
Alternative codes found
RIV/00216224:14310/18:00111730
Result on the web
<a href="http://dx.doi.org/10.1002/cctc.201701490" target="_blank" >http://dx.doi.org/10.1002/cctc.201701490</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cctc.201701490" target="_blank" >10.1002/cctc.201701490</a>
Alternative languages
Result language
angličtina
Original language name
Flavin Photocatalysts for visible Light [2+2] Cycloadditions: Structure, Reactivity and Reaction Mechanism
Original language description
New photocatalysts from the flavin family were found to mediate the [2+2] photocycloaddition reaction. 3-Butyl-10-methyl-5-deazaflavin (3a) and 1-butyl-7,8-dimethoxy-3-methylalloxazine (2e), if irradiated by visible light, were shown to allow an efficient (Phi approximate to 3-10%) intramolecular cyclisation of various types of substrates including substituted styrene dienes and bis(aryl enones), considered as electron-rich and electron-poor substrates, respectively, without any additional reagent. The versatility of the procedure was demonstrated by the cyclisation of photosensitive cinnamyl (E)-3-iodoallyl ether. Structure-activity studies found alloxazine 2e was more active than 7-monosubstituted (R = Cl, Br and MeO) alloxazines. The introduction of chlorine and bromine atom on the deazaflavin skeleton did not enhance the catalytic efficiency of 3a. A detailed electrochemical and spectroscopic study explains the reaction mechanism proceeding through energy transfer from the flavin excited triplet state to the diene followed by its cyclisation.
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
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
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
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Volume of the periodical
10
Issue of the periodical within the volume
4
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
849-858
UT code for WoS article
000425626700026
EID of the result in the Scopus database
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