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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 4: 1198 - 1209

DOI: https://doi.org/10.6023/cjoc202110042

ARTICLES

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

  • Yurong Zhang ,
  • Han Wang ,
  • Yongjun Mao ,
  • Shiliang Shi
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  • 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
* E-mail: ;

Received date: 2021-10-29

  Revised date: 2021-11-28

  Online published: 2021-12-02

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)

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Abstract

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

Cite this article

Yurong Zhang , Han Wang , Yongjun Mao , Shiliang Shi . Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1198 -1209 . DOI: 10.6023/cjoc202110042

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