%0 Journal Article %T Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and N H-sulfoximines %+ Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB) %+ Unité de Recherche de Chimie Médicinale et Environnementale [Université de Sfax] %+ Institut Universitaire de France (IUF) %A Guilbaud, Johan %A Labonde, Marine %A Selmi, Awatef %A Kammoun, Majed %A Cattey, Hélène %A Pirio, Nadine %A Roger, Julien %A Hierso, Jean-Cyrille %Z CNRS Universite de Bourgogne Conseil Regional de Bourgogne (JCE PhD grant) through the plan d'actions regional pour l'innovation (PARI) fonds europeen de developpement regional (FEDER) programs ANR-PRC 2016 program (ALCATRAS) %< avec comité de lecture %@ 1566-7367 %J Catalysis Communications %I Elsevier %V 111 %P 52 - 58 %8 2018-06 %D 2018 %R 10.1016/j.catcom.2018.03.025 %K thiols %K efficient %K arenes %K sulfides %K indoles %K Thiolates %K Palladium %K C-S coupling %K Resting state %K Sulfones %K NH-sulfoximines %K H functionalization %K directing group %K bond formation %K s-arylation %K acid salts %Z Chemical Sciences %Z Physics [physics]Journal articles %X 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. %G English %L hal-01857091 %U https://u-bourgogne.hal.science/hal-01857091 %~ UNIV-BOURGOGNE %~ CNRS %~ ICMUB %~ INC-CNRS %~ TEST-HALCNRS %~ TEST2-HALCNRS