可见光催化CO2参与异腈的1,1-双官能团化羧基化反应

doi:10.1016/S1872-2067(26)65211-4

催化学报 ›› 2026, Vol. 91: 93-102.DOI: 10.1016/S1872-2067(26)65211-4

可见光催化CO₂参与异腈的1,1-双官能团化羧基化反应

蒋元旭^a^,¹, 严志鑫^b^,¹, 王珑富^b, 陈奕驰^a, 徐文浩^a, 张淑荣^b, 岳峻平^a, 潘敏^a, 贵永远^b, 宋磊^c^,^*(), 廖黎丽^d^,^*(), 叶剑衡^a, 余达刚^a^,^e^,^*()

^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 四川师范大学化学与材料科学学院, 四川成都 610068
^c 四川大学碳中和未来技术学院, 四川成都 610065
^d 四川大学华西公共卫生学院(华西第四医院), 四川成都 610041
^e 南开大学元素有机化学国家重点实验室, 天津 300071

收稿日期:2026-02-22 接受日期:2026-05-09 出版日期:2026-12-18 发布日期:2026-10-13
通讯作者: ^*电子信箱: lsong@scu.edu.cn (宋磊),
liaolili94@scu.edu.cn (廖黎丽),
dgyu@scu.edu.cn (余达刚).
作者简介:¹共同第一作者.
基金资助:
国家重点研发计划(2024YFA1509702);国家自然科学基金(22225106);国家自然科学基金(22501189);四川省科技计划(2024NSFSC0027);四川省科技计划(2025ZNSFSC0908);四川省科技计划(2025ZNSFSC0911);中央高校基本科研业务费

Visible-light photocatalytic 1,1-difunctionalizing carboxylation of isocyanides with CO₂

Yuan-Xu Jiang^a^,¹, Zhi-Xin Yan^b^,¹, Long-Fu Wang^b, Yi-Chi Chen^a, Wen-Hao Xu^a, Shu-Rong Zhang^b, Jun-Ping Yue^a, Min Pan^a, Yong-Yuan Gui^b, Lei Song^c^,^*(), Li-Li Liao^d^,^*(), Jian-Heng Ye^a, Da-Gang Yu^a^,^e^,^*()

^a Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
^b College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, Sichuan, China
^c College of Carbon Neutrality Future Technology, Sichuan University, Chengdu 610065, Sichuan, China
^d West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu 610041, Sichuan, China
^e State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received:2026-02-22 Accepted:2026-05-09 Online:2026-12-18 Published:2026-10-13
Contact: ^*E-mail: lsong@scu.edu.cn (L. Song),
liaolili94@scu.edu.cn (L.-L. Liao),
dgyu@scu.edu.cn (D.-G. Yu).
About author:¹Contributed equally to this work.
Supported by:
National Key R&D Program of China(2024YFA1509702);National Natural Science Foundation of China(22225106);National Natural Science Foundation of China(22501189);Sichuan Science and Technology Program(2024NSFSC0027);Sichuan Science and Technology Program(2025ZNSFSC0908);Sichuan Science and Technology Program(2025ZNSFSC0911);Fun-damental Research Funds for the Central Universities

摘要/Abstract

摘要：

CO₂作为一种储量丰富、廉价易得、低毒可再生的C1资源, 其高值化有机转化受到了广泛关注. 近年来, CO₂参与不饱和化合物的催化双官能团化羧基化反应发展迅速, 为构建结构多样的羧酸化合物提供了高效途径. 其中, 基于单电子转移过程形成的CO₂或不饱和化合物自由基负离子中间体, 由于具有独特的反应活性与选择性, 在CO₂参与的羧基化反应中得到了广泛应用. 目前, 相关研究主要集中于不饱和化合物的1,2-双官能团化羧基化或氢羧基化反应, 而1,1-双官能团化羧基化反应仍鲜有报道. 因此, 发展基于自由基负离子策略的CO₂参与不饱和化合物的1,1-双官能团化羧基化反应, 对于拓展CO₂化学及发展新型自由基反应模式具有重要意义.
可见光催化凭借其反应条件温和、环境友好以及优异的官能团兼容性等优势, 已成为构建复杂有机分子的重要手段. 基于此, 本文通过可见光驱动硫酚催化策略, 实现了CO₂参与异腈的1,1-双官能团化羧基化反应, 在温和条件下高效构建了一系列重要的N-杂芳烃羧酸化合物. 该策略通过硫酚负离子与异腈形成电子给体-受体复合物, 在可见光激发下发生复合物分子内单电子转移, 生成异腈自由基负离子中间体, 并进一步与CO₂发生羧基化反应. 该反应具有良好的底物适用范围和官能团兼容性, 可兼容卤素、醚、硫醚、酯基等多种官能团, 高效构建菲啶羧酸、苯并噻唑羧酸及苯并硒唑羧酸等具有重要价值的N-杂芳烃羧酸骨架. 同时, 该方法表现出良好的克级放大反应效果及后续衍生转化能力, 展现出较好的合成应用潜力. 此外, 本文综合运用自由基捕获实验、氘代实验、亲电试剂捕获实验、紫外-可见吸收光谱和循环伏安测试等机理实验, 并结合理论计算, 对反应机理进行了系统研究. 结果表明, 硫酚负离子与异腈形成的电子给体-受体复合物在可见光照射下发生单电子转移, 生成兼具亲核性与还原性的异腈自由基负离子中间体, 同时释放硫自由基. 根据异腈与CO₂氧化还原电位及中间体稳定性的差异, 反应可能经历不同的羧基化路径: 当异腈的氧化还原电位高于CO₂时, 异腈自由基负离子直接对CO₂发生亲核进攻, 形成羧基化亚胺自由基中间体; 当异腈的氧化还原电位低于CO₂时, 异腈自由基负离子则优先将CO₂还原为CO₂自由基负离子, 后者再对异腈发生自由基加成, 也将形成羧基化亚胺自由基中间体; 对于氧化还原电位与CO₂相近的异腈底物, 两种路径可能同时存在. 羧基化亚胺自由基中间体进一步经历分子内自由基环化及氢原子转移过程生成目标产物.
综上, 本文基于自由基负离子反应策略, 拓展了CO₂参与不饱和化合物羧基化反应的研究范畴, 在温和条件下实现了可见光促进硫酚催化异腈与CO₂的1,1-双官能团化羧基化反应, 为发展自由基负离子介导的CO₂选择性羧基化反应提供了新的设计思路.

关键词: 二氧化碳, 可见光催化, 自由基负离子, 电子给体-受体复合物, 1,1-双官能团化羧基化

Abstract:

Difunctionalizing carboxylation of unsaturated compounds with CO₂ has emerged as a powerful strategy for synthesizing functionalized carboxylic acids. While substantial progress has been made, existing approaches have predominantly focused on 1,2-difunctionalizing carboxylation processes. Herein, we report the first 1,1-difunctionalizing carboxylation of isocyanides with CO₂, enabling the efficient construction of diverse N-heteroaromatic carboxylic acids under mild conditions. This visible-light photocatalytic protocol displays broad substrate scope, good functional group tolerance, ready scalability and facile late-stage derivatization. Mechanistic studies and density functional theory calculations reveal that the generated electron-donor-acceptor complex could facilitate the formation of isocyanide- or CO₂-derived radical anions, according to their redox potentials and stability. These radical anion intermediates could undergo following carboxylation to afford diverse N-heteroaromatic carboxylic acids.

Key words: Carbon dioxide, Visible-light photocatalysis, Radical anion, Electron-donor-acceptor complex, 1,1-Difunctionalizing carboxylation

蒋元旭, 严志鑫, 王珑富, 陈奕驰, 徐文浩, 张淑荣, 岳峻平, 潘敏, 贵永远, 宋磊, 廖黎丽, 叶剑衡, 余达刚. 可见光催化CO₂参与异腈的1,1-双官能团化羧基化反应[J]. 催化学报, 2026, 91: 93-102.

Yuan-Xu Jiang, Zhi-Xin Yan, Long-Fu Wang, Yi-Chi Chen, Wen-Hao Xu, Shu-Rong Zhang, Jun-Ping Yue, Min Pan, Yong-Yuan Gui, Lei Song, Li-Li Liao, Jian-Heng Ye, Da-Gang Yu. Visible-light photocatalytic 1,1-difunctionalizing carboxylation of isocyanides with CO₂[J]. Chinese Journal of Catalysis, 2026, 91: 93-102.

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图/表 8

Fig. 1. Schematic illustration of radical anion-involved carboxylation with CO2.

Table 1 Optimization of the reaction conditions a.

Table 2 Substrate scope of biphenyl isocyanides a.

Table 3 Substrate scope of 2-isocyanoaryl thioethers and selenides a.

Scheme 1. Schematic illustration for synthetic transformations including gram-scale synthesis and late-stage derivatization.

Scheme 2. Mechanistic investigations of the photocatalytic carboxylation reaction.

Scheme 3. Computational studies. All energies are in kcal mol-1 and represent the relative free energies calculated at the B3LYP/6-311+G(d,p)/SMD(DMAc)//B3LYP/6-31+G(d)/SMD(DMAc) level of theory. The bond lengths are reported in angstroms (Å).

Scheme 4. Proposed plausible reaction mechanism for the 1,1-difunctionalizing carboxylation of isocyanides with CO2.

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可见光催化CO₂参与异腈的1,1-双官能团化羧基化反应

Visible-light photocatalytic 1,1-difunctionalizing carboxylation of isocyanides with CO₂

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