A chromatographic relay conjugated photoredox strategy: S, Se-pharmacophore from alkenes via formal [2+2+1] heteroannulation

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00599754" target="_blank" >RIV/61388963:_____/24:00599754 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1039/D4CC03527E" target="_blank" >https://doi.org/10.1039/D4CC03527E</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4cc03527e" target="_blank" >10.1039/d4cc03527e</a>

Result language
angličtina
Original language name
A chromatographic relay conjugated photoredox strategy: S, Se-pharmacophore from alkenes via formal [2+2+1] heteroannulation
Original language description
An expedient route to 2-aminodihydrothiophenes and their seleno analogues is reported. A three-component photoredox reaction between alkene, thio(seleno)cyanate, and bromomalonate is employed, generating a carbo-thio(seleno)cyanate intermediate that undergoes a domino of reactions mediated by alumina column chromatography, leading to valuable chalcogen pharmacophores. Mechanistic investigations using DFT and control experiments reveals an intramolecular H-bond responsible for driving the domino forward.
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
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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