Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1198-1209.DOI: 10.6023/cjoc202110042 Previous Articles     Next Articles



张玉荣a,b, 王晗a,*(), 茆勇军a, 施世良a,b,*()   

  1. a 上海工程技术大学化学化工学院 上海 201620
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2021-10-29 修回日期:2021-11-28 发布日期:2021-12-02
  • 通讯作者: 王晗, 施世良
  • 基金资助:
    国家自然科学基金(21690074); 国家自然科学基金(21871288); 国家自然科学基金(91856111); 国家自然科学基金(21821002); 国家自然科学基金(22171280); 中国科学院战略性先导科技专项(XDB20000000)

Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids

Yurong Zhanga,b, Han Wanga(), Yongjun Maoa, Shiliang Shia,b()   

  1. a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032
  • Received:2021-10-29 Revised:2021-11-28 Published:2021-12-02
  • Contact: Han Wang, Shiliang Shi
  • Supported by:
    National Natural Science Foundation of China(21690074); National Natural Science Foundation of China(21871288); National Natural Science Foundation of China(91856111); National Natural Science Foundation of China(21821002); National Natural Science Foundation of China(22171280); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)

A Ni-catalyzed three-component coupling reaction of alkenylboronic acids, aldimines, and 1,3-butadiene for rapid synthesis of homoallylic amines bearing a skipped diene moiety is disclosed. This reaction represents a rare example for modular 1,4-dicarbofunctionalization of 1,3-butadiene, an abundant feedstock chemical. This protocol furnishes a diverse variety of (E)-homoallylic amines in high yields with excellent regio- and stereo-selectivity. The mild and base-free reaction condition enables excellent functional group tolerance and broad scope for aldimine and alkenylboronic acid coupling partners.

Key words: skipped diene, nickel catalysis, butadiene, multicomponent reaction, coupling, homoallylic amine