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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ACS Omega

ISSN

2470-1343

e-ISSN

2470-1343

Svazek periodika

9

Číslo periodika v rámci svazku

46

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

46148-46156

Kód UT WoS článku

001347530100001

EID výsledku v databázi Scopus

2-s2.0-85209224904