Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species

Abstract

A visible light-induced vicinal diazidation of various alkenes using stable sulfonium bis(acetoxy)iodate(I) and sodium azide as a radical precursor is described. The trimethylsulfonium [bis(azido)iodate(I)] species, intrinsically generated in situ, demonstrated unprecedented reactivity toward CC π bond-promoting selective azidation under photochemical conditions without any photoredox or metal catalyst. The visible-light stimulated diazidation reaction provides a convenient and straightforward approach to highly prevalent vicinal nitrogen scaffolds of myriad therapeutic importance.