Sau, Subham and Das, Krishna Mohan and Mondal, Bijan and Thakur, Arunabha (2024) Cobalt(II)-Catalyzed Synthesis of γ-Diketones from Aryl Alkenes and Its Utilization in the Synthesis of Various Heterocyclic Compounds. JOURNAL OF ORGANIC CHEMISTRY, 89 (10). pp. 7095-7108. ISSN 0022-3263, 1520-6904
Full text not available from this repository. (Request a copy)Abstract
An earth-abundant Co(II) salt-catalyzed mild and affordable synthetic route has been developed for the synthesis of industrially relevant 1,4-dicarbonyl compounds (or gamma-diketones) via oxidative coupling between aryl alkenes and ketones (both cyclic and acyclic) using TBHP and DBU as the oxidant and base, respectively. 1,4-Dicarbonyl compounds are known to be synthesized using expensive metal catalysts, dual catalysts, or low-cost metal complexes combined with an additive or ligand template, which further needs to be synthesized. Herein, we report the synthesis of 1,4-dicarbonyl compounds using cobalt(II) acetate as a catalyst without any expensive co-catalyst or ligand templates. This methodology has a broad substrate scope with significant yields and good functional group tolerance. Generation of unsymmetrical 1,4-dicarbonyls at room temperature and its versatile synthetic expansion to produce synthetically and biologically valuable heterocyclic compounds are salient features of this novel methodology. In addition, various controlled experiments such as primary kinetic isotope effect study, Hammett analysis with variation of the nature of the substituents on the styrene ring, and theoretical calculations (density functional theory) unravel the mechanistic intricacies involved in this new, simple, and atom-economic methodology.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SILYL ENOL ETHERS; 1,4-DICARBONYL COMPOUNDS; SIMPLE ALKANES; BASIS-SET; ACCESS; ALDEHYDES; LIGHT; ESTERS; HYDROACYLATION; 1,4-DIKETONES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 04 Dec 2025 08:36 |
| Last Modified: | 04 Dec 2025 08:36 |
| URI: | https://pred.uni-regensburg.de/id/eprint/64474 |
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