Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2319-2325.DOI: 10.6023/cjoc202012020 Previous Articles     Next Articles



李琳琳a, 陈晓雨a, 裴聪聪a, 李敬亚b, 邹大鹏a,*(), 吴养洁a,*(), 吴豫生a,b,*()   

  1. a 郑州大学化学学院 绿色催化中心 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:2020-12-12 修回日期:2021-03-02 发布日期:2021-03-22
  • 通讯作者: 邹大鹏, 吴养洁, 吴豫生
  • 基金资助:
    国家自然科学基金(21172200); 国家自然科学基金(21702191)

Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B2pin2/D2O System

Linlin Lia, Xiaoyu Chena, Congcong Peia, Jingya Lib, Dapeng Zoua(), Yangjie Wua(), Yusheng Wua,b()   

  1. a College of Chemistry, Green Catalysis Center, Zhengzhou University, Zhengzhou 450052
    b Tetranov Biopharm, Limited Liability Company, Zhengzhou 450052
  • Received:2020-12-12 Revised:2021-03-02 Published:2021-03-22
  • Contact: Dapeng Zou, Yangjie Wu, Yusheng Wu
  • Supported by:
    National Natural Science Foundation of China(21172200); National Natural Science Foundation of China(21702191)

A transition metal-free deuteride reduction protocol of N-tert-butanesulfinyl ketimines with B2pin2 has been developed. After screening of reaction parameters, such as base, solvent, and the amount of B2pin2, a series of deuterated secondary amines were obtained in reasonable yields with excellent deuterium purity by using D2O as the deuterium source. Mild reaction conditions, operational simplicity, and easily scaled up to gram scale are the considerable advantages of this methodology. After deprotection of tert-butanesulfinyl, cyclopentan-1-d-amine is obtained in high yield.

Key words: deuteride reduction, N-tert-butanesulfinyl ketimines, bis(pinacolate)diboron, deuterated secondary amines