Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds

Here we have demonstrated a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion leading to highly substituted imidazoles and privileged dihydroisoquinoline-based imidazole derivatives via C(sp(3))-H and C-(sp(2))-H bond functionalization. A sustainable, convenient, metalfree azidation/C-H aminative cyclization approach in the absence of stoichiometric oxidants is presented. This protocol involves a rare photoinduced iminyl radical as a key intermediate for the N insertion.

Automated summary

This study demonstrates a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion for the synthesis of highly substituted imidazoles and dihydroisoquinoline-based imidazole derivatives via functionalization of C(sp(3))-H and C-(sp(2))-H bonds. The sustainable and convenient metal-free azidation/C-H aminative cyclization approach without stoichiometric oxidants involves a rare photoinduced iminyl radical as a key intermediate for the N insertion.