Synthesis of α-Hydroxy and α-Alkoxy Esters Enabled by a Visible-Light-Induced O–H Insertion Reaction of Diazo Compounds
Chao Yang, Wujiong Xia, Jinrui Bai, Dan Qi, Zhuoheng Song, Bin Li, Lin Guo
Abstract
Abstract A visible-light-induced O–H insertion reaction of diazo compounds is reported. This synthetic method, unlike conventional pathways, does not rely on transition metals, Lewis acids, or Brønsted acids; does not use any catalyst; and produces valuable α-hydroxy and α-alkoxy esters in good yields of up to 98%. The protocol exhibits a broad substrate scope and good functional-group tolerance. Notably, a gram-scale synthesis has been performed in a photochemical continuous-flow mode.
Topics & Concepts
ChemistryDiazoAlkoxy groupSubstrate (aquarium)Lewis acids and basesFunctional groupCatalysisInsertion reactionCombinatorial chemistryVisible spectrumReaction conditionsPhotochemistryStereochemistryMedicinal chemistryOrganic chemistryAlkylPolymerGeologyPhysicsOptoelectronicsOceanographyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions