伯胺在电催化媒介ABNO作用下的自氧化偶联反应

Electrocatalytic Oxidative Coupling of Primary Amines with the Medium ABNO

以9-氮杂双环[3.3.1]壬烷-N-氧基自由基(ABNO)为电催化媒介,在NaClO4-MeCN溶液中伯胺通过自氧化偶联反应生成对应的亚胺.采用循环伏安法研究了ABNO对伯胺的电催化性能.在相同条件下,与2,2,6,6-四甲基哌啶氮氧自由基相比,ABNO在伯胺的自氧化偶联反应中表现出更好的电催化反应活性.采用电化学原位红外光谱技术分析其中间产物为Ph—CH=NH.在优化的反应条件下,一系列芳香伯胺可在ABNO电催化作用下自氧化偶联生成对应的亚胺,产率较高.

In the NaClO4 MeCN solution,an electrochemical oxidative coupling of primary amines was developed with the electrocatalytic medium 9 azabicyclo[3.3.1]nonane N oxyl(ABNO).The electrocatalytic performance of ABNO for the primary amines was studied by cyclic voltammetry.As compared with 2,2,6,6 tetramethylpiperidine nitroxyl radical under similar conditions,ABNO showed higher electrocatalytic perfor mance in the oxidation coupling reaction.The Ph—CH NH was analyzed as the intermediate by electro chemical in situ FTIR.Under the optimized conditions,a series of aromatic primary amines underwent the electrochemical oxidative coupling to form corresponding imines in good to excellent yields with the ABNO as the electrocatalytic medium.