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2019 , Vol. 39 >Issue 7: 2001 - 2008

DOI: https://doi.org/10.6023/cjoc201902011

研究论文

B2pin2参与的含硼酸酯的芳香胺和醛的一锅两步还原胺化反应

  • 刘雪滢 ,
  • 刘振伟 ,
  • 郭圆圆 ,
  • 李敬亚 ,
  • 邹大鹏 ,
  • 吴豫生 ,
  • 吴养洁
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  • a 郑州大学化学与分子工程学院 郑州 450052;
    b 郑州泰基鸿诺医药股份有限公司 郑州 450052

收稿日期: 2019-02-13

  修回日期: 2019-03-15

  网络出版日期: 2019-03-29

基金资助

国家自然科学基金（Nos.21172200，21702191）资助项目.

收起

One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B2pin2 as Reductant

  • Liu Xueying ,
  • Liu Zhenwei ,
  • Guo Yuanyuan ,
  • Li Jingya ,
  • Zou Dapeng ,
  • Wu Yusheng ,
  • Wu Yangjie
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  • a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
    b Tetranov Biopharm, Limited Liability Company, Zhengzhou 450052

Received date: 2019-02-13

  Revised date: 2019-03-15

  Online published: 2019-03-29

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172200, 21702191).

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摘要

官能团化的仲胺广泛存在于生物和天然产物，在有机化学中具有重要的地位.此外，含硼酸频哪醇酯的芳香仲胺是一种重要的有机合成中间体.研究了在氢氧化钠和乙醇的存在下，联硼酸频哪醇酯作为还原剂，含硼酸频哪醇酯的芳香伯胺和醛的一锅两步还原胺化反应.通过对碱、温度、溶剂、时间、醛的用量等进行筛选，在较优的反应条件下以中等到较好的收率得到了一系列相应的含硼酸频哪醇酯的芳香仲胺.该方法产率较高，具有良好的官能团容忍性，并且合成的芳香仲胺中硼酸频哪醇酯取代基还可以进一步官能团化.

关键词： 还原胺化; 含硼的芳香仲胺; 联硼酸频哪醇酯; 醛

本文引用格式

刘雪滢 , 刘振伟 , 郭圆圆 , 李敬亚 , 邹大鹏 , 吴豫生 , 吴养洁 . B2pin2参与的含硼酸酯的芳香胺和醛的一锅两步还原胺化反应[J]. 有机化学, 2019 , 39(7) : 2001 -2008 . DOI: 10.6023/cjoc201902011

Abstract

The aromatic amine functionality occupies a very important role in organic chemistry due to its prominence in biological and naturally occurring molecules. In addition, the synthesized secondary aromatic amines with pendant boronate ester are versatile intermediates in several organic transformations. The one-pot, two-step reductive amination of boron-containing primary aromatic amines and aldehydes has been achieved in the presence of NaOH in ethanol using B2pin2 as reductant. After extensive screening of various reaction parameters, such as base, reaction temperature, solvent, reaction time and protective gas, a series of secondary aromatic amines with pendant boronate ester and various functional groups were obtained in moderate to good yields under the optimal reaction conditions. This system features generally high yields and broad functional group tolerance. The boronate ester substituent is a very good handle to be further functionalized.

Key words： reductive amination; boron-containing secondary aromatic amines; bis (pinacolato) diboron; aldehydes

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