Ni(0)-Catalyzed Efficient, Regioselective Synthesis of Dibenzo[b,e]oxepines and Dibenzo[c,f][1,2]oxathiepine 6,6-Dioxides: Mechanistic Study by DFT Calculation and Docking Interactions

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00601638" target="_blank" >RIV/61388963:_____/24:00601638 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1021/acsomega.4c06569" target="_blank" >https://doi.org/10.1021/acsomega.4c06569</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsomega.4c06569" target="_blank" >10.1021/acsomega.4c06569</a>

Result language
angličtina
Original language name
Ni(0)-Catalyzed Efficient, Regioselective Synthesis of Dibenzo[b,e]oxepines and Dibenzo[c,f][1,2]oxathiepine 6,6-Dioxides: Mechanistic Study by DFT Calculation and Docking Interactions
Original language description
Herein, a nickel-catalyzed divergent reductive-Heck reaction of 1-bromo-2-((2-(aryl/alkyl ethynyl)phenoxy)methyl)benzene and 2-(aryl/alkyl ethynyl)phenyl 2-bromobenzenesulfonate derivatives has been demonstrated through the regulation of reducing agents and solvent systems. This scalable protocol offers regio- and stereoselective access to functionalized dibenzo[b,e]oxepine and dibenzo[c,f][1,2]oxathiepine 6,6-dioxide scaffolds in high to excellent yields under a mild set of reaction conditions. This methodology offers a predictable route for the synthesis of medium ring oxygen heterocycles and demonstrates wide substrate scope and outstanding tolerance to various functional groups like hydroxyl and, of course, practical instance via the synthesis of doxepin and nordoxepin molecules. We validate the experimentally proposed reaction mechanism using the density functional theory method. Further, molecular docking interactions were investigated accommodating some of our synthesized molecules.
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
10403 - Physical 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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