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Visible-Light-Driven Unsymmetric <i>gem</i>-Difunctionalization of Vinyl Azides with Thiosulfonates or Selenosulfonates

Tao Wang, Yuan-Yuan Zong, Biao Yang, Tao Huang, Xiaoling Jin, Qiang Liu

2024Organic Letters22 citationsDOI

Abstract

Thiosulfonylation and selenosulfonylation of vinyl azides with thiosulfonates and selenosulfonates were achieved using Cu(dap) 2 Cl as a photosensitizer under visible-light irradiation. This reaction is the application of a vinyl azide substrate in a group transfer radical addition (GTRA) reaction, through β-difunctionalization, to obtain a variety of unsymmetric difunctionalized N-unprotected enamines.

Topics & Concepts

ChemistryPolymer chemistryCombinatorial chemistryPhotochemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods