二氧化碳参与的自由基型烯烃双官能团化反应

doi:10.6023/A19060208

化学学报 ›› 2019, Vol. 77 ›› Issue (9): 783-793.DOI: 10.6023/A19060208 上一篇下一篇

所属专题：有机自由基化学

研究展望

二氧化碳参与的自由基型烯烃双官能团化反应

张振^a^b, 龚莉^b, 周晓渝^b, 颜思顺^b, 李静^b^*(), 余达刚^b^*()

^a成都大学药学与生物工程学院农业农村部杂粮加工重点实验室成都 610106
^b四川大学化学学院绿色化学与技术教育部重点实验室成都 610064

投稿日期:2019-06-12 发布日期:2019-07-12
通讯作者: 李静,余达刚 E-mail:jingli@scu.edu.cn;dgyu@scu.edu.cn
作者简介:张振, 特聘副研究员, 1985年出生于山西怀仁市, 2007年在四川大学化学学院获得学士学位, 2017年在中科院成都有机所获得博士学位(导师: 支永刚研究员和余达刚教授), 随后在成都大学药学与生物工程学院工作至今. 其研究兴趣主要是药物合成、二氧化碳化学.|李静, 助理研究员, 1981年出生于四川广安市, 2006年在四川大学化学学院获得学士学位, 2009年在四川大学化学学院获得硕士学位(导师: 余孝其教授), 随后在四川抗菌素工业研究所工作至2012年, 2012年6月在四川大学化学学院工作至今. 其研究兴趣主要是二氧化碳化学、无机-有机杂化材料的合成.|余达刚, 2007年本科毕业于四川大学化学学院, 2012年博士毕业于北京大学化学与分子工程学院(导师: 施章杰教授), 2012~2014年作为洪堡学者在德国明斯特大学(导师: Frank Glorius教授)开展博士后研究, 2015年回到四川大学开展教学和独立研究工作, 被聘为教授、博士生导师. 主要从事二氧化碳利用和可见光催化等绿色可持续发展化学研究, 已发表学术论文60余篇, 参与攥写英文专著2个章节, 受邀在国内外会议上做邀请报告和主题报告10余次. 曾入选2015年中组部“青年千人”、四川省“青年千人”和2016年“Organic Chemistry Frontiers” Emerging Investigators; 主持了2018年国家自然科学基金委优秀青年基金和霍英东青年教师基金等多项科研项目; 曾获得2017年Thieme Chemistry Journal Award、2017年ACP Lectureship Awards、2018年中国化学会青年化学奖、2018年四川大学“优秀教师”等奖励.
基金资助:
项目受科技部“973”(No.2015CB856600);国家自然科学基金(Nos.21822108);国家自然科学基金(21801025);教育部霍英东基金(No.161013);中央高校基本业务费资助

Radical-Type Difunctionalization of Alkenes with CO₂

Zhang, Zhen^a^b, Gong, Li^b, Zhou, Xiao-Yu^b, Yan, Si-Shun^b, Li, Jing^b^*(), Yu, Da-Gang^b^*()

^aKey Laboratory of Coarse Cereal Processing (Ministry of Agriculture and Rural Affairs), College of Pharmacy and Biological Engineering, Chengdu University, Chengdu 610106
^bKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received:2019-06-12 Published:2019-07-12
Contact: Li, Jing,Yu, Da-Gang E-mail:jingli@scu.edu.cn;dgyu@scu.edu.cn
Supported by:
Project supported by the “973” Project from the Ministry of Science and Technology of China(No.2015CB856600);the National Natural Science Foundation of China(Nos.21822108);the National Natural Science Foundation of China(21801025);the Fok Ying Tung Education Foundation(No.161013);the Fundamental Research Funds for the Central Universities.

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摘要/Abstract

二氧化碳(CO₂)是一种理想的C1合成子. 利用其参与化学转化合成羧酸和含羰基杂环等具有高附加值的产品, 具有重要意义. 另一方面, 烯烃的双官能团化反应是有机合成化学中的一类重要反应, 可以将简单易得的烯烃快速高效地转化为结构多样性的重要化合物. 然而, 由于CO₂反应活性较低, 而且烯烃官能团化反应的选择性难以控制, CO₂参与的烯烃双官能团化反应具有较高的挑战性. 近年来, 自由基化学的蓬勃发展为该类反应的开发提供了新的策略, 实现了一些重要转化反应. 基于此, 从CO₂参与烯烃的氧-烷基化反应、碳羧基化反应、硅羧基化反应、硫羧基化反应以及双羧基化反应等反应入手, 全面总结和深入分析了最近几年CO₂参与的自由基型烯烃双官能团化反应进展; 在介绍上述进展的同时, 重点阐述了其可能经历的四类自由基化学历程. 最后对该领域的未来发展方向进行了展望, 希望为该领域的进一步发展提供一些思路.

关键词: 二氧化碳, 烯烃, 双官能团化, 自由基, 可见光催化

CO₂ is an ideal C1 source in chemical transformations. It is of great significance to utilize CO₂ in chemical conversion to synthesize high value-added compounds, including carboxylic acids and carbonyl-containing heterocycles. On the other hand, the difunctionalization of olefins is an important organic reaction, which can efficiently convert easily available olefins into important compounds with structural diversity. However, due to the low reactivity of CO₂ and the difficulty in controlling the selectivity, the difunctionalization of olefins with CO₂ is highly challenging. Recently, the significant progress of radical chemistry has provided new strategies and promoted the development of novel transformations in this field. This Perspective summarizes the recent progress of the radical-type difunctionalization of olefins with CO₂, including the oxy-alkylation, carbocarboxylation, silacarboxylation, thiocarboxylation, and dicarboxylation of alkenes with CO₂. At the same time, we also highlight the mechanism with radicals and four kinds of pathways are proposed: (1) Free radicals attack olefins to form new carbon radical intermediates. The radicals are then oxidized to form carbocations, which are further captured by carbonates or carbamates. It is also possible for direct C—O bonding reaction or sequent C—I and C—O bonds formation. (2) The new carbon radical intermediates, in-situ generated through attack of alkenes with radicals, are reduced via single electron transfer into carbanions, which could attack CO₂to form C—C bonds. (3) CO₂is reduced into CO₂ radical anions in the highly reductive reaction conditions. Once generated, the CO₂ radical anions might attack olefins to form carboxylate bearing more stable carbon radical intermediates (such as benzylic ones) and further form C—C bonds or carbon-heteroatom bonds. (4) Olefins are reduced via single electron transfer into alkenyl free radical anions in the highly reductive reaction conditions. These anions may attack CO₂to form carboxylate bearing carbon radical intermediates and are further reduced to generate carbanions. Finally they may attack another CO₂to form succinic acid derivatives. We point out the challenges and predict the future development in the field, including the more challenging substrates, more reaction types, better selectivities, and deeper mechanistic understanding.

Key words: carbon dioxide, olefin, difunctionalization, radical, visible-light photoredox catalysis

引用此文

张振, 龚莉, 周晓渝, 颜思顺, 李静, 余达刚. 二氧化碳参与的自由基型烯烃双官能团化反应[J]. 化学学报, 2019, 77(9): 783-793.

Zhang, Zhen, Gong, Li, Zhou, Xiao-Yu, Yan, Si-Shun, Li, Jing, Yu, Da-Gang. Radical-Type Difunctionalization of Alkenes with CO₂[J]. Acta Chimica Sinica, 2019, 77(9): 783-793.

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图/表 15

图1. 二氧化碳参与的自由基型烯烃双官能团化反应

Figure 1. Radical-type difunctionalization of alkenes with CO2

图2. CO2参与的烯丙胺的氧-三氟甲基化

Figure 2. Selective oxytrifluoromethylation of allylamines with CO2

图3. CO2参与的自由基型去芳构化反应

Figure 3. Radical trifluoromethylative dearomatization of indoles and furans with CO2

图4. CO2参与的烯丙胺的氧-全氟烷基化反应

Figure 4. Carboxylative cyclization of allyl amines with CO2

图5. CO2参与的烯丙醇的氧-全氟烷基化反应

Figure 5. Carboxylative cyclization of allyl alcohols with CO2

图6. CO2参与的烯丙胺的氧-二氟烷基化

Figure 6. Oxy-difluoroalkylation of allylamines with CO2

图7. 可见光驱动钯催化的烯丙胺的氧-烷基化反应

Figure 7. Oxy-alkylation of allylamines via visible-light-driven palladium catalysis

图8. CO2参与的烯烃双官能团化反应

Figure 8. Dicarbofunctionalization of styrenes with CO2

图9. CO2参与的芳基烯烃碳羧基化反应机理

Figure 9. A proposed mechanism of dicarbofunctionalization of styrenes with CO2 and radical precursors

图10. CO2参与的烯烃与硅烷或烷烃的双官能团化反应

Figure 10. Dicarbofunctionalization of alkenes with CO2 and silanes or alkanes

图11. CO2参与的烯烃与硅烷或烷烃的双官能团化反应机理

Figure 11. A proposed mechanism of dicarbofunctionalization of alkenes with CO2 and silanes or alkanes

图12. 可见光驱动铁促进CO2参与的烯烃与苯硫酚的硫羧基化反应

Figure 12. Visible-light-driven iron-promoted thiocarboxylation of alkenes with CO2

图13. 可见光驱动铁促进CO2参与的烯烃与苯硫酚的硫羧基化反应机理

Figure 13. A proposed mechanism of visible-light-driven iron-promoted thiocarboxylation of alkenes with CO2

图14. Senboku和Tokuda组电催化CO2参与的烯烃双羧基化反应

Figure 14. Electrosynthesis of 2-phenylsuccinic acids with CO2 by Senboku and Tokuda group

图15. 江焕峰课题组电催化CO2参与烯烃和1,3-丁二烯的双羧基化反应

Figure 15. Electrochemical dicarboxylation of arylalkenes and 1,3-dienes with CO2 by Jiang group

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二氧化碳参与的自由基型烯烃双官能团化反应

Radical-Type Difunctionalization of Alkenes with CO₂

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二氧化碳参与的自由基型烯烃双官能团化反应

Radical-Type Difunctionalization of Alkenes with CO2

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Radical-Type Difunctionalization of Alkenes with CO₂