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Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and N H-sulfoximines

Abstract : We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium-1,1'-bis [(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium catalyzed C-S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C-S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C-S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol-isolated and characterized by multinuclear NMR and XRD-with both 2-chloropyridine and 2-bromopyridine.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01857091
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : mardi 14 août 2018 - 10:56:33
Dernière modification le : mardi 23 juin 2020 - 12:30:05

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Johan Guilbaud, Marine Labonde, Awatef Selmi, Majed Kammoun, Hélène Cattey, et al.. Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and N H-sulfoximines. Catalysis Communications, Elsevier, 2018, 111, pp.52 - 58. ⟨10.1016/j.catcom.2018.03.025⟩. ⟨hal-01857091⟩

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