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2023 , Vol. 43 >Issue 5: 1868 - 1874

DOI: https://doi.org/10.6023/cjoc202209039

研究论文

1,2-迁移促进的苄基季铵盐硼化反应研究

  • 秦玉承 ,
  • 徐良轩 ,
  • 徐佳能 ,
  • 刘超
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  • a 中国科学院兰州化学物理研究所 羰基合成与选择性氧化国家重点实验室 兰州 730000
    b 中国科学院大学 北京 100049

收稿日期: 2022-09-30

  修回日期: 2022-11-16

  网络出版日期: 2022-12-21

基金资助

国家自然科学基金(22022113)

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1,2-Migration Enabled Borylation of Benzylic Quaternary Ammonium

  • Yucheng Qin ,
  • Liangxuan Xu ,
  • Jianeng Xu ,
  • Chao Liu
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  • a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
    b University of Chinese Academy of Sciences, Beijing 100049
* Corresponding author. E-mail:

Received date: 2022-09-30

  Revised date: 2022-11-16

  Online published: 2022-12-21

Supported by

National Natural Science Foundation of China(22022113)

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摘要

报道了一种无过渡金属参与的季铵盐硼化反应, 通过1,2-硼迁移的模式, 使用苄基季铵盐为底物, 大位阻碱[双(三甲基硅烷基)氨基钾, 缩写为KHMDS]作为攫氢试剂, B2pin2作为硼源, 同时使用不同的淬灭方式可以得到一系列苄基单硼和苄基偕二硼化合物. 反应具有很好的底物普适性以及官能团兼容性, 同时, 可应用于克级反应的制备.

关键词： 苄基季铵盐; 硼化; 苄基硼酸酯; 1,2-迁移

本文引用格式

秦玉承 , 徐良轩 , 徐佳能 , 刘超 . 1,2-迁移促进的苄基季铵盐硼化反应研究[J]. 有机化学, 2023 , 43(5) : 1868 -1874 . DOI: 10.6023/cjoc202209039

Abstract

A transition metal-free borylation of quaternary ammonium salts has been reported via a 1,2-boronate migrations using benzyl quaternary ammonium salts as substrates and base (potassium bis(trimethylsilyl)amide, KHMDS) with steric hinderance as hydrogen abstractor, B2pin2 as the boron source. In this transformation, benzylic monoboronate esters and benzylic 1,1-diboronate esters can be obtained by different quenching methods. This transformation showed a favorable tolerance for benzylic quaternary ammonium with different functional groups. A gram scale synthesis was performed.

Key words： benzylic quaternary ammonium; borylation; benzylboronic esters; 1,2-migration

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