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Electrochemical 2,2,6,6-tetramethylpiperidinyl- N -oxyl (TEMPO)-Mediated α -Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions

2021; Science Press; Volume: 41; Issue: 8 Linguagem: Inglês

10.6023/cjoc202103049

0253-2786

Jun-Qing Gao, Xin‐Jun Weng, Cong Ma, Xue-Tao Xu, Ping Fang, Tian‐Sheng Mei,

Radical Photochemical Reactions

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 α-aminonitriles and α-amino phosphonates under mild conditions.Preliminary study indicated that the formation of the product was through the Shono oxidation of imine species.