镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应

doi:10.6023/cjoc202110042

有机化学 ›› 2022, Vol. 42 ›› Issue (4): 1198-1209.DOI: 10.6023/cjoc202110042 上一篇下一篇

研究论文

镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应

张玉荣^a^,^b, 王晗^a^,^*(), 茆勇军^a, 施世良^a^,^b^,^*()

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 Zhang^a^,^b, Han Wang^a(), Yongjun Mao^a, Shiliang Shi^a^,^b()

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)

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摘要/Abstract

发展了一种镍催化的烯基硼酸、亚胺和1,3-丁二烯的三组分偶联反应, 用于高效合成含有1,4-二烯结构的高烯丙基胺类化合物. 该反应的原料均简单易得, 其中1,3-丁二烯是大宗化工产品. 该过程实现了少有报道的1,3-丁二烯的1,4-双碳化反应. 反应以优秀的区域选择性和立体选择性, 高收率地合成了一系列(E)-高烯丙基胺产物, 简单温和、无外加碱的反应条件使该方法具有广泛的底物范围和优秀的官能团兼容性.

关键词: 1,4-二烯, 镍催化, 丁二烯, 多组分反应, 偶联, 高烯丙基胺

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

引用此文

张玉荣, 王晗, 茆勇军, 施世良. 镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应[J]. 有机化学, 2022, 42(4): 1198-1209.

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.

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图/表 7

Scheme 1. Examples of natural products containing homoallylic amines and approaches to homoallylic amines

Scheme 2. Examples of skipped dienes in natural products, and synthetic method to skipped dienes

Table 1. Optimization of the reaction conditions

Table 2. Scope of aldiminesa

Table 3. Scope of organoboronic acids

Scheme 3. Gram-scale reaction, tandem coupling-lactamization, and isoprene-imine coupling

Scheme 4. Proposed catalytic cycle

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镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应

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

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