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2024 , Vol. 44 >Issue 3: 1013 - 1020

DOI: https://doi.org/10.6023/cjoc202309022

研究论文

电化学促使α-重氮酯的磷酸化构筑亚膦酸腙

  • 孙雪 ,
  • 颜廷涛 ,
  • 闫克鲁 ,
  • 杨建静 ,
  • 文江伟
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  • 曲阜师范大学化学与化工学院 山东省高校绿色天然产物与医药中间体重点实验室 山东曲阜 273165
共同第一作者

收稿日期: 2023-09-21

  修回日期: 2023-11-13

  网络出版日期: 2023-11-23

基金资助

国家自然科学基金(21902083); 山东省自然科学基金(ZR2020QB130); 曲阜师范大学人才启动基金(6132); 曲阜师范大学人才启动基金(6125)

收起

Electrochemical Enabled Phosphorylation of α-Diazoester to Access Phosphinic Hydrazone

  • Xue Sun ,
  • Tingtao Yan ,
  • Kelu Yan ,
  • Jianjing Yang ,
  • Jiangwei Wen
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  • Key Laboratory of Green Natural Products and Pharmaceutical Intermediates in Colleges and Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
The authors contributed equally to this work.
*E-mail: ;

Received date: 2023-09-21

  Revised date: 2023-11-13

  Online published: 2023-11-23

Supported by

National Natural Science Foundation of China(21902083); Natural Science Foundation of Shandong Province(ZR2020QB130); Talent Program Foundation of Qufu Normal University(6132); Talent Program Foundation of Qufu Normal University(6125)

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摘要

亚膦酸腙是一种罕见的结构片段, 有望应用于医药、功能材料、配体和合成中间体. 报道了一种牺牲阳极镍电极形成Ni2＋以促进α-重氮酯磷酸化构筑亚膦酸腙的电化学方法. 反应在恒电流下进行, 无需外加贵金属催化剂和化学氧化还原试剂, 具有良好的底物适用性. 机理研究证实了成对电解介导的催化机制占主导地位.

关键词： 电化学; 牺牲阳极; 磷酸化; α-重氮酯; 亚磷酸腙

本文引用格式

孙雪 , 颜廷涛 , 闫克鲁 , 杨建静 , 文江伟 . 电化学促使α-重氮酯的磷酸化构筑亚膦酸腙[J]. 有机化学, 2024 , 44(3) : 1013 -1020 . DOI: 10.6023/cjoc202309022

Abstract

The phosphonic hydrazone represents a rare molecular fragment with promising applications in the fields of pharmaceuticals, functional materials, ligands, and synthetic intermediates. A novel electrochemical approach is presented for the generation of Ni2＋ ions from sacrificial anode nickel, facilitating the phosphorylation of α-diazoester to construct phosphite hydrazone. The reaction was performed in an undivided cell in absence of precious metal catalyst and chemical redox reagent, exhibiting good substrate applicability. The mechanistic investigation has confirmed the predominant role of paired electrolysis in mediating the catalytic mechanism.

Key words： electrochemistry; sacrificial anode; phosphorylation; α-diazoester; phosphinic hydrazine

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