Work

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

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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.

Source: ACS Omega

DOI: 10.1021/acsomega.4c06569

Authors: Uma Sankar Mandal, Sk Shamim Ahamed, Rabindranath Lo, Debashree Manna, Tapas Ghosh

Institutions: Jadavpur University, Czech Academy of Sciences, Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Council of Scientific and Industrial Research, India, Science and Engineering Research Board