Arylation of perfluoroalkyl vinyl sulfoxides via the Heck reaction

Liubov V. Sokolenko (1) , Yurii L. Yagupolskii (1) , Yurii G. Vlasenko (1) , Liudmila N. Babichenko (2) , Volidimir O. Lipetskij (3) , Elsa Anselmi (4, 5) , Emmanuel Magnier (5)

1 Institute of Organic Chemistry
2 ChemBioCenter
3 Enamine Ltd
4 UMR ISP - Infectiologie et Santé Publique
5 UVSQ - Université de Versailles Saint-Quentin-en-Yvelines

Heck reactions of perfluoroalkyl vinyl sulfoxides with aryl iodides are studied and palladium(II) acetate is shown to be the most convenient catalyst for this process. New E-1-aryl-2-perfluoroalkylsulfinylethylenes are synthesized. In all cases, by-products without a perfluoroalkylsulfinyl group are formed.

Mots clés: Heck reaction; Vinylation; Cross-coupling; Palladium; Vinyl sulfoxides; sulfones; palladium(ii); sulfides; ligands

Domaines: Sciences du Vivant [q-bio]

Liubov V. Sokolenko, Yurii L. Yagupolskii, Yurii G. Vlasenko, Liudmila N. Babichenko, Volidimir O. Lipetskij, et al.. Arylation of perfluoroalkyl vinyl sulfoxides via the Heck reaction. Tetrahedron Letters, 2015, 56 (10), pp.1259-1262. ⟨10.1016/j.tetlet.2015.01.136⟩. ⟨hal-01170057⟩