New oxidative reactions of monovinylsilanes with sulfonamides

• Oxidative sulfamidation of vinylsilanes is studied; • Triphenyl(vinyl)silane with triflamide and NaOI gives the product of bistriflamidation; • Dichloromethyl(vinyl)silane with triflamide and NaOI gives the product of desilylation; • Triphenyl(vinyl)silane with sulfonamides and NBS affords bromoamidines; • Bromoamidines are quantitatively dehydrobrominated to imidazolines; The reactions of sulfonamidation of functionally substituted vinylsilanes having Si–Ph, Si–Cl or Si–O bonds (triphenylvinylsilane, trimethoxy(vinyl)silane, trichlorovinylsilane, dichloromethylvinylsilane, tris(2-methoxyethoxy)vinylsilane) with trifluoromethanesulfonamide, arenesulfonamides and methanesulfonamide in the presence of ( t -BuOCl + NaI) or N -bromosuccinimide proceed in different manner depending on the substrate, reagent, and oxidant. The formation of the products of halosulfonamidation, heterocyclization, halogenation, solvent interception and desilylation is observed.