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General Synthesis of Alkenyl Sulfides by Palladium-Catalyzed Thioetherification of Alkenyl Halides and Tosylates

Noelia Velasco, Cintia Virumbrales, Roberto Sanz, Samuel Suárez-Pantiga* and Manuel A. Fernández-Rodríguez*

*Universidad de Alcalá, 28805, Alcalá de Henares-Madrid, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain, Email: mangel.fernandezruah.es, svsuarezubu.es

N. Velasco, C. Virumbrales, R. Sanz, S. Suárez-Pantiga, M. A. Fernández-Rodríguez, Org. Lett., 2018, 20, 2848-2852.

DOI: 10.1021/acs.orglett.8b00854 (free Supporting Information)


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Abstract

Palladium complexes derived from inexpensive dppf ligand catalyze the cross-coupling reaction of alkenyl bromides with thiols under low catalyst loading. These reactions occur in high yields and display wide scope, including the coupling of bulky thiols and trisubstituted bromoolefins, and functional group tolerance. In addition, a thioetherification of less reactive chloroalkenes and alkenyl tosylates has also been achieved.

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Key Words

vinyl sulfides


ID: J54-Y2018