Visible Light‐Induced [3+2] Cyclization Reactions of Hydrazones with Hypervalent Iodine Diazo Reagents for the Synthesis of 1‐Amino‐1,2,3‐Triazoles
Dong Jun-ying, He Wang, Shukuan Mao, Xin Wang, Mingdong Zhou, Lei Li
Abstract
Abstract In this study, visible‐light‐induced [3+2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents as diazomethyl radical precursors are reported. Mild reaction conditions, a broad substrate scope, and excellent functional group compatibility were observed. Furthermore, the synthetic utility was demonstrated by gram‐scale synthesis and elaboration to several value‐added products. This protocol broadens the scope of diazo chemistry, and is applicable to the late‐stage functionalization of natural products. magnified image
Topics & Concepts
Hypervalent moleculeDiazoChemistryReagentCombinatorial chemistryFunctional groupIodineSubstrate (aquarium)Visible spectrumOrganic chemistryPolymerOceanographyOptoelectronicsPhysicsGeologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions