Work

Direct halo-/seleno-sulfonylation and diselenylation of ynamides mediated by visible light

Year: 2026

Type: article

Abstract: Blue LED light-induced double functionalization of ynamides in the presence of tosyl iodide, tosyl bromide, tosyl phenyl selenide, tosyl benzyl selenide, and diphenyl diselenide is reported. The strategy, based on the photoinduced cleavage of the tosyl derivatives (TsY), or diselenide derivative, involves radical addition to the triple bond of ynamides followed by atom/group transfer. It allows the increase of molecular complexity in a simple, clean, and atom economical manner. These atom-transfer-radical-addition (ATRA) processes occur in the absence of initiator or catalyst with high yield and high regio- and stereoselectivity leading to complex tetrasubstituted alkenes bearing no less than three heteroatoms. Theoretical support to the mechanism and the scope and limitation of the reaction are discussed.

Source: RSC Advances

DOI: 10.1039/d6ra04323b