Visible-Light-Mediated Dual Functionalization of Allenes: Regio- and Stereoselective Synthesis of Vinylsulfone Azides

A gentle and effective method for the photocatalytic dual functionalization of allenes with high regio- and stereoselectivity using a nonmetallic catalyst is described. Inexpensive and easily available sulfinates and TMSN3 were employed as sulfone and azido sources, respectively. The method is characterized by satisfactory substrate compatibility and tolerance toward functional groups. The straightforward initial mechanistic experiments suggested that the reaction could follow a radical pathway. The synthesis of vinylsulfone azide derivatives presented here offers a promising scaffold for the future development of vinyl sulfone-based drugs and functional bioorthogonal reagents.