Regioselective Wacker-Type Oxidation of Internal Olefins in <sup><i>t</i></sup>BuOH Using Oxygen as the Sole Oxidant and <sup><i>t</i></sup>BuONO as the Organic Redox Cocatalyst
Qing Huang, Yawei Li, Xiao‐Shan Ning, Guo-Qing Jiang, Xiaowei Zhang, Jian‐Ping Qu, Yan‐Biao Kang
Abstract
A regioselective Wacker–Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good yields with high regioselectivities.
Topics & Concepts
ChemistryRegioselectivityOxygenWacker processRedoxMedicinal chemistryCatalysisOrganic chemistryPalladiumOxidative Organic Chemistry ReactionsChemical Synthesis and ReactionsSynthetic Organic Chemistry Methods