基于1,3-二烯的自由基反应的近期研究进展

doi:10.1016/S1872-2067(21)63919-0

催化学报 ›› 2022, Vol. 43 ›› Issue (3): 548-557.DOI: 10.1016/S1872-2067(21)63919-0

• 可见光催化有机合成专栏 • 上一篇下一篇

基于1,3-二烯的自由基反应的近期研究进展

王芃梓^a, 肖文精^a, 陈加荣^a^,^b^,^*()

^a华中师范大学化学学院, 华师-渥太华大学联合研究中心, 农药与化学生物学教育部重点实验室, 湖北武汉 430079
^b河南师范大学化学与化工学院, 河南新乡 453007

收稿日期:2021-06-29 修回日期:2021-06-29 接受日期:2021-08-10 出版日期:2022-03-18 发布日期:2022-02-18
通讯作者: 陈加荣
基金资助:
国家自然科学基金(91856119);国家自然科学基金(21971081);国家自然科学基金(21820102003);国家自然科学基金(91956201);河南师范大学化学学科开放基金(2021YB02);华中师范大学优博培育计划(王芃梓);高等学校学科创新引智计划(111项目);高等学校学科创新引智计划(B17019)

Recent advances in radical-mediated transformations of 1,3-dienes

Peng-Zi Wang^a, Wen-Jing Xiao^a, Jia-Rong Chen^a^,^b^,^*()

^aCCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, China
^bSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, Henan, China

Received:2021-06-29 Revised:2021-06-29 Accepted:2021-08-10 Online:2022-03-18 Published:2022-02-18
Contact: Jia-Rong Chen
Supported by:
National Natural Science Foundation of China(91856119);National Natural Science Foundation of China(21971081);National Natural Science Foundation of China(21820102003);National Natural Science Foundation of China(91956201);Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University(2021YB02);Excellent Doctoral Dissertation Cultivation Grant to Peng-Zi Wang from CCNU;Program of Introducing Talents of Discipline to Universities of China(111项目);Program of Introducing Talents of Discipline to Universities of China(B17019)

摘要/Abstract

摘要：

有机自由基化学的发展可追溯到110多年前. 起初, 高活性的自由基中间体被认为是难以控制且不可预测的物种, 往往导致反应变得杂乱无章, 这种误解导致该领域的研究没有得到足够的重视. 为了发展高效、高选择性且符合绿色化学要求的化学转化, 合成化学家们一直致力于开发新颖的催化体系和反应试剂, 而自由基化学因其独特的反应性质和巨大的发展潜力也逐渐引起人们的广泛关注. 与离子型物种相比, 自由基物种在拓展反应类型、提升反应兼容性以及快速构筑分子复杂性方面具有显著优势. 伴随着这一领域的快速发展, 自由基化学已逐渐取得了许多不错的突破和进展. 如今, 自由基反应已经作为有机合成中一类重要反应, 在化学键的断裂与重建过程以及构建功能分子方面具有不可替代性. 如何进一步拓展自由基前体和丰富自由基受体仍是合成化学家们长期追求的目标.
随着自由基化学的发展, 不饱和体系的自由基官能化反应也取得了重大进展. 相较于普通烯烃, 1,3-二烯作为一类易从石油化工生产获取, 且用途广泛的大宗化学品, 在合成化学中具有重要应用潜力, 其参与的自由基官能化反应是一类极具价值的合成转化反应. 基于这类反应人们不仅可以同时引入两个不同的结构片段, 而且产物中的另一个双键可以通过进一步转化引入更多的官能团. 因此, 这类反应在构建分子复杂性和多官能化分子方面具有独特的优势. 近年来, 过渡金属催化与有机自由基化学的有效结合极大地推动了1,3-二烯自由基相关反应的发展, 并取得了一些令人瞩目的研究进展. 另外, 可见光驱动的光氧化还原催化的发展也为这一领域提供了新的发展方向, 通过选择合适的自由基前体和可见光催化体系可以实现一系列1,3-二烯的1,2-或1,4-双官能化产物合成. 此外, 光催化和金属催化结合的协同催化模式也为这类反应的立体选择性控制提供了可能.
本综述根据自由基前体和反应类型, 简要总结了近期1,3-二烯参与的自由基转化的最新研究进展, 并选取一些代表性反应, 对其底物适用性和机理研究进行着重探讨和分析, 同时针对该领域目前存在的问题以及未来的发展方向进行了讨论和展望.

关键词: 自由基反应, 1,3-二烯, 自由基双官能化, 过渡金属催化, 光氧化还原催化

Abstract:

1,3-Dienes are a class of easily accessible and versatile feedstock chemicals that can participate in a wide range of reactions to facilitate the synthesis of various valuable allylic compounds. In the past decades, radical methodology has emerged as a powerful tool for organic synthesis by virtue of the fact that diverse highly reactive radical species can usually be generated under mild, neutral and controlled conditions, and allow for rapid generation of molecular complexity. In this review, we critically illustrate the recent advances in the field of radical-mediated transformations of 1,3-dienes based on the different radical precursors and working modes. Wherever possible, particular emphasis is also put on the related mechanistic studies and synthetic applications.

Key words: Radical transformations, 1,3-Dienes, Radical difunctionalization, Transition metal catalysis, Photoredox catalysis

王芃梓, 肖文精, 陈加荣. 基于1,3-二烯的自由基反应的近期研究进展[J]. 催化学报, 2022, 43(3): 548-557.

Peng-Zi Wang, Wen-Jing Xiao, Jia-Rong Chen. Recent advances in radical-mediated transformations of 1,3-dienes[J]. Chinese Journal of Catalysis, 2022, 43(3): 548-557.

图/表 21

Fig. 1. Radical-mediated transformations of 1,3-dienes.

Scheme 1. Cobalt-catalyzed three-component coupling reaction of alkyl halides, 1,3-dienes, and trimethylsilylmethyl magnesium chloride.

Scheme 2. Copper-catalyzed regioselective 1,2-alkylesterification of 1,3-dienes to allylic esters.

Scheme 3. Copper-catalyzed radical-mediated Heck-type alkylation of 1,3-dienes.

Scheme 4. Enantioselective 1,2-difunctionalization of 1,3-butadienes by a Cr/Co bimetallic catalysis system.

Scheme 5. Copper-catalyzed asymmetric diamination of 1,3-dienes.

Scheme 6. Copper-catalyzed 1,2-amino oxygenation of 1,3-dienes with O?acylhydroxylamines and carboxylic acids.

Scheme 7. Intermolecular [3 + 2] cycloadditions of aryl cyclopropyl ketone with 1,3-diene by tandem Lewis acid and photoredox catalysis.

Scheme 8. Dialkylation of 1,3-dienes by dual photoredox and chromium catalysis.

Scheme 9. Photoredox Ni-catalyzed branch-selective reductive coupling between aldehydes with 1,3-dienes.

Scheme 10. Three-component allylation of carbonyls with 1,3-butadiene and alkyl halides via π-allyltitanium complexes.

Scheme 11. Visible-light-driven enantioselective radical carbocyanation of 1,3-dienes via photocatalytic generation of allylcopper complexes.

Scheme 12. Visible-light-induced photoredox-catalyzed decarboxylative alkyl-esterification with 1,3-dienes.

Scheme 13. Photoinduced copper-catalyzed asymmetric radical C-O cross-coupling of 1,3-dienes and ketone oxime esters.

Scheme 14. Photoinduced Pd-catalyzed three-component radical 1,2-aminoalkylation of 1,3-dienes.

Scheme 15. Visible-light-driven photocatalyzed radical amidoarylation of 1,3-butadiene.

Scheme 16. Selective 1,2-aminoisothiocyanation of 1,3-dienes under visible-light-driven photoredox catalysis.

Scheme 17. Photo-sensitized oxy-thiocyanation of 1,3-aryldienes.

Scheme 18. A mild hydroaminoalkylation of 1,3-dienes using a dual cobalt and photoredox catalytic system.

Scheme 19. Visible-light-driven photoredox catalyzed addition of tertiary carbon radicals to electron-deficient 1,3-dienes.

Scheme 20. Visible-light photoredox catalyzed radical 1,4-carbonfunctionlization of 1,3-dienes via π-allylpalladium complexes.

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基于1,3-二烯的自由基反应的近期研究进展

Recent advances in radical-mediated transformations of 1,3-dienes

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