Copper(I)-Catalyzed Aerobic Oxidation of α-Diazoesters
Changming Xu, Yong Wang, Lei Bai
Abstract
A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.
Topics & Concepts
ChemistryVicinalBond cleavageMolecular oxygenArylCatalysisDiazoOxidative phosphorylationCleavage (geology)CopperCombinatorial chemistryOxidative cleavageMedicinal chemistryOrganic chemistryBiochemistryEngineeringAlkylGeotechnical engineeringFracture (geology)Cyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions