Styrene derivatives reacted with diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1) at low temperature to afford 2-arylethenyl(diphenyl)sulfonium triflates (2). Treatment of 2 with primary amines gave the corresponding 2-arylaziridines in high yields. One-pot synthesis of various aziridines was also successfully carried out without isolation of the intermediate 2.
1,1-Disubstituted and trisubstituted alkenes were converted into the corresponding β,γ-unsaturated amines 4 via three steps: the initial formation of α,β-unsaturated diphenylsulfonium triflates 2 from alkenes and diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1), followed by double bond migration of 2 to β,γ-unsaturated sulfonium triflates 3 with primary or secondary amines, and successive nucleophilic substitution of 3 with these amines.
Reactions of diphenylvinylsulfonium triflates with primary amines and imides afforded 2-arylaziridines and α-imidostyrenes, respectively. These products were also obtained from styrenes in one vessel without isolation of the intermediate sulfonium salts. In addition, 1,1-disubstituted and trisubstituted alkenes were converted into allylamines via isomerization of initially formed vinylsulfonium salts to allylsulfonium salts in the presence of primary or secondary amines.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.