Synergistic Catalysis of Se and Cu for the Activation of <scp><i>α</i>‐H</scp> of Methyl Ketones with Molecular Oxygen/Alcohol to Produce <scp><i>α</i>‐Keto</scp> Acetals<sup>†</sup>
Chao Chen, Zhicheng Cao, Xu Zhang, Yiming Li, Lei Yu, Xuefeng Jiang
Abstract
Summary of main observation and conclusion Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α ‐keto acetals directly. Using O 2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O 2 to allow the key rearrangement and selenoxide syn ‐elimination regenerating the catalytically active organoselenium species.
Topics & Concepts
ChemistryCatalysisReagentAlcoholSolventSeleniumCopperOxygenMedicinal chemistryOrganic chemistryOrganoselenium and organotellurium chemistrySulfur-Based Synthesis TechniquesVanadium and Halogenation Chemistry