Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp<sup>3</sup>)–H and C(sp<sup>2</sup>)–H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds
Srilaxmi M. Patel, Ermiya Prasad P., Manickam Bakthadoss, Duddu S. Sharada
Abstract
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(sp3)–H and C(sp2)–H bond functionalization. A sustainable, convenient, metal-free 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.
Topics & Concepts
ChemistrySurface modificationImidazolePhotocatalysisNitrogenVisible spectrumPhotochemistryMedicinal chemistryStereochemistryCatalysisOrganic chemistryOptoelectronicsPhysical chemistryMaterials scienceRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques