Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2001-2008.DOI: 10.6023/cjoc201902011 Previous Articles     Next Articles

Articles

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a, 刘振伟a, 郭圆圆a, 李敬亚b, 邹大鹏a, 吴豫生b, 吴养洁a   

  1. 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 出版日期:2019-07-25 发布日期:2019-03-29
  • 通讯作者: 邹大鹏, 吴豫生, 吴养洁 E-mail:yusheng.wu@tetranovglobal.com;wyj@zzu.edu.cn;zdp@zzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21172200,21702191)资助项目.

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

Liu Xueyinga, Liu Zhenweia, Guo Yuanyuana, Li Jingyab, Zou Dapenga, Wu Yushengb, Wu Yangjiea   

  1. a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
    b Tetranov Biopharm, Limited Liability Company, Zhengzhou 450052
  • Received:2019-02-13 Revised:2019-03-15 Online:2019-07-25 Published:2019-03-29
  • Contact: 10.6023/cjoc201902011 E-mail:yusheng.wu@tetranovglobal.com;wyj@zzu.edu.cn;zdp@zzu.edu.cn
  • Supported by:

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

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