Ong, Chiu Ling and Tang, Wai Kit and Khaligh, Nader Ghaffari and Juan, Joon Ching (2024) One-pot thermo-induced radical-radical oxidative cross-coupling for symmetrical dimeric thiadiazole monosulfide formation. Journal of Molecular Structure, 1301. ISSN 0022-2860, DOI https://doi.org/10.1016/j.molstruc.2023.137389.
Full text not available from this repository.Abstract
The production of heterocyclic sulfide is the key building block in various applications, especially in the field of medicinal chemistry. Currently, heterocyclic sulfide was synthesized via deoxygenation of sulfoxide or cross coupling between sulfur sources and halogen compounds. However, these conventional methods suffer from drawbacks such as the use of toxic solvents, harsh reaction conditions, the requirement for transition metal catalysts, inert conditions, and the generation of toxic and corrosive halide-containing waste. In this study, a milder approach using hydrogen peroxide-mediated oxidative cross-coupling of 5-alkylsulfanyl-1,3,4thiadiazole-2-thiol successfully produces symmetrical dimeric thiadiazole monosulfide with an isolated yield of 73‒87 %. The molecular structure of bis(2-octylsulfanyl-1,3,4thiadiazolyl)-5,5′-sulfide was confirmed by X-ray crystal structure analysis. Interestingly, the formation of dimeric thiadiazole monosulfide undergoes a one-pot thermo-induced pathway. Density functional theory (DFT) indicates the formation of thiadiazole monosulfide is thermodynamically favorable through the cross-coupling reaction between thiadiazole thiyl radical and thiadiazole carbon-centered radical. © 2023
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Uncontrolled Keywords: | Catalysts; Chemical bonds; Density functional theory; Metal halides; Organic compounds; Sulfur compounds; Synthesis (chemical); Transition metals; Building blockes; Cross-couplings; C‒S coupling; Medicinal chemistry; Monosulfide; One pot; Radical-radical oxidative cross-coupling; Symmetrical dimeric thiadiazole monosulphide; Thermo-induced; Thiadiazoles; Crystal structure |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry Nanotechnology & Catalysis Research Centre |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 11 Jul 2024 04:16 |
| Last Modified: | 11 Jul 2024 04:16 |
| URI: | http://eprints.um.edu.my/id/eprint/44743 |
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