可见光催化二氧化碳参与非活化烯烃1,3-双羧基化反应

doi:10.1016/S1872-2067(23)64468-7

催化学报 ›› 2023, Vol. 50: 222-228.DOI: 10.1016/S1872-2067(23)64468-7

可见光催化二氧化碳参与非活化烯烃1,3-双羧基化反应

肖汉至^a^,¹, 于博^a^,^b^,¹, 颜思顺^a, 章炜^a, 李茜茜^a, 鲍莹^a, 罗书平^c, 叶剑衡^a^,^*(), 余达刚^a^,^*()

^a四川大学化学学院, 绿色化学与技术教育部重点实验室, 四川成都 610064
^b中国科学院青岛生物能源与过程研究所, 山东能源研究院, 山东青岛 266101
^c浙江工业大学绿色化学合成技术国家重点实验室, 浙江杭州 310014

收稿日期:2023-04-18 接受日期:2023-05-22 出版日期:2023-07-18 发布日期:2023-07-25
通讯作者: *电子信箱: jhye@scu.edu.cn (叶剑衡), dgyu@scu.edu.cn (余达刚).
作者简介:
¹共同第一作者.
基金资助:
国家自然科学基金(22225106);国家自然科学基金(22101191);中国博士后科学基金(2020M683301);中国博士后科学基金(2021M692261);四川大学基础研究基金(2020SCUNL102);四川省科技计划(2021YJ0405);中央高校基本科研业务费专项金资助

Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂

Han-Zhi Xiao^a^,¹, Bo Yu^a^,^b^,¹, Si-Shun Yan^a, Wei Zhang^a, Xi-Xi Li^a, Ying Bao^a, Shu-Ping Luo^c, Jian-Heng Ye^a^,^*(), Da-Gang Yu^a^,^*()

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
^bShandong Energy Institute, CAS Key Laboratory of Bio-based Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, Shandong, China
^cState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, Zhejiang, China

Received:2023-04-18 Accepted:2023-05-22 Online:2023-07-18 Published:2023-07-25
Contact: *E-mail: jhye@scu.edu.cn (J.-H. Ye), dgyu@scu.edu.cn (D.-G. Yu).
About author:
¹ Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22225106);National Natural Science Foundation of China(22101191);China Postdoctoral Science Foundation(2020M683301);China Postdoctoral Science Foundation(2021M692261);Fundamental Research Funds from Sichuan University(2020SCUNL102);Sichuan Science and Technology Program(2021YJ0405);Fundamental Research Funds for the Central Universities

摘要/Abstract

摘要：

二氧化碳(CO₂)具有储量丰富、廉价易得、无毒可再生的特点, 是一种理想的碳一合成子. 在CO₂参与的众多转化中, 合成应用广泛、易于衍生的羧酸化学品具有较高的研究价值. 其中, 有机二元羧酸是一种重要的化学品, 广泛应用于材料加工、有机合成和生物医药等领域. 尽管目前CO₂参与的单羧基化反应研究取得了较大进展, 但CO₂参与构建的区域选择性二羧基化反应方法仍然亟待发展. 近年来, 可见光化学因其具有绿色温和、官能团兼容性较好等特点已成为利用CO₂构建二羧基化反应的有力策略. 目前虽已发展了不同策略实现了烯烃1,1-, 1,2-, 1,6-和1,7-双羧基化等不同的区域选择性, 但现有策略还未能完成烯烃1,3-双羧基化的区域选择性. 另外, 现有策略仅能构建两个C-C键.

本文利用可见光催化策略, 基于1,2-芳基迁移过程, 在温和条件下实现了CO₂参与非活化烯烃1,3-双羧基化反应, 实现了双羧基化领域尚未实现的区域选择性. 反应过程涉及一个C-C单键断裂和三个C-C单键形成, 可合成一系列新型戊二酸类产物, 并且产物易于衍生为杂环结构. 一系列给电子、吸电子取代基以及杂芳环取代基均能兼容于反应体系. 机理实验结果表明, 反应中可原位产生二氧化碳自由基阴离子(CO₂^•‒), 随后经历自由基加成、1,2-芳基迁移、单电子还原和亲核进攻CO₂等过程产生二元羧酸产物. 综上, 本文为可见光催化CO₂参与二羧基化反应方法提供了重要的区域选择性补充, 并可同时构建多个C-C键, 具有应用前景.

关键词: 二氧化碳, 可见光催化, 1,3-双羧基化, 非活化烯烃, 1,2-芳基迁移

Abstract:

Photocatalytic carboxylation with CO₂ is a powerful strategy for the synthesis of functionalized carboxylic acids and their derivatives under mild conditions. However, the dicarboxylation of alkenes with CO₂ is still underdeveloped and confined to the formation of only two C-C bonds. Herein, we report the 1,3-dicarboxylation of unactivated alkenes with CO₂ via 1,2-aryl migration, which involves the cleavage of one C-C bond and the formation of three C-C bonds. This visible-light photocatalytic protocol is also distinguished by good functional group tolerance, broad substrate scope, and facile derivations of products to heterocyclic scaffolds. Mechanistic studies indicate that the in situ generated formate could act as the radical precursor of CO₂˙ˉ, and the following radical addition, 1,2-aryl migration, single electron reduction, and nucleophilic attack at the second CO₂ would afford the dicarboxylic acids.

Key words: Carbon dioxide, Visible-light photocatalysis, 1,3-Dicarboxylation, Unactivated alkene, 1,2-Aryl migration

肖汉至, 于博, 颜思顺, 章炜, 李茜茜, 鲍莹, 罗书平, 叶剑衡, 余达刚. 可见光催化二氧化碳参与非活化烯烃1,3-双羧基化反应[J]. 催化学报, 2023, 50: 222-228.

Han-Zhi Xiao, Bo Yu, Si-Shun Yan, Wei Zhang, Xi-Xi Li, Ying Bao, Shu-Ping Luo, Jian-Heng Ye, Da-Gang Yu. Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂[J]. Chinese Journal of Catalysis, 2023, 50: 222-228.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(23)64468-7

https://www.cjcatal.com/CN/Y2023/V50/I7/222

图/表 7

Fig. 1. State-of-the-art of visible light-driven dicarboxylations of alkenes with CO2.

Table 1 Optimization of reaction conditions a.

Table 2 Test of different substituents on the allylic position. a

Table 3 Scope of α,α-diaryl allylic amides.a

Scheme 1. Facile transformations of 2a.

Scheme 2. Mechanistic investigations.

Scheme 3. Plausible reaction mechanism.

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可见光催化二氧化碳参与非活化烯烃1,3-双羧基化反应

Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂

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可见光催化二氧化碳参与非活化烯烃1,3-双羧基化反应

Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO2

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Photocatalytic 1,3-dicarboxylation of unactivated alkenes with CO₂