Electrochemical 2,2,6,6-tetramethylpiperidinyl-<i>N</i>-oxyl (TEMPO)-Mediated <i>α</i>-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions
Jun-Qing Gao, Xin‐Jun Weng, Cong Ma, Xue-Tao Xu, Ping Fang, Tian‐Sheng Mei
Abstract
Metal-free electrochemical oxidation cyanation and phosphonylation reactions had been developed, in which 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO) reduced the electrode potential of substrate and avoided over oxidation of some electron rich aromatic amines under electrochemical conditions. This protocol had good functional group compatibility, which made it to be a practical and efficient method to synthesize -aminonitriles and -amino phosphonates under mild conditions. Preliminary study indicated that the formation of the product was through the Shono oxidation of imine species.
Topics & Concepts
ChemistryElectrochemistryCyanationMetalPolymer chemistryOrganic chemistryElectrodePhysical chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques