1174014-07-3Relevant academic research and scientific papers
Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines
Guilbaud, Johan,Labonde, Marine,Selmi, Awatef,Kammoun, Majed,Cattey, Hélène,Pirio, Nadine,Roger, Julien,Hierso, Jean-Cyrille
, p. 52 - 58 (2018/04/11)
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.
2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes
Garcia-Rubia, Alfonso,Fernandez-Ibanez, M. Ungeles,Gomez Arrayas, Ramon,Carretero, Juan Carlos
supporting information; experimental part, p. 3567 - 3570 (2011/05/12)
Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.
Efficient copper(I)-catalyzed C-S cross-coupling of thiols with aryl halides in an aqueous two-phase system
Zhang, Xin-Yan,Zhang, Xiao-Yan,Guo, Sheng-Rong
experimental part, p. 23 - 35 (2011/12/05)
A mild and convenient C-S bond formation reaction catalyzed by CuI/L-proline in an aqueous two-phase system was achieved, providing a simple method for the synthesis of aryl sulfides in good yields.
Catalyst-free and base-free water-promoted SNAr reaction of heteroaryl halides with thiols
Sreedhar,Surendra Reddy,Amarnath Reddy
experimental part, p. 1732 - 1738 (2009/12/26)
A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products. Georg Thieme Verlag Stuttgart.
