基于配体-金属电荷转移的铁催化光致脱羧官能团化反应

doi:10.6023/cjoc202505025

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3517-3533.DOI: 10.6023/cjoc202505025 上一篇下一篇

综述与进展

基于配体-金属电荷转移的铁催化光致脱羧官能团化反应

张晨晨^a, 丁清杰^a, 吕琪妍^b^,^c, 马春华^a^,^*(), 姜玉钦^a^,^*(), 於兵^b^,^*()

^a 河南师范大学化学化工学院河南新乡 453007
^b 郑州大学化学学院郑州 450001
^c 南京林业大学林木生物质低碳高效利用国家工程研究中心南京 210037

收稿日期:2025-05-22 修回日期:2025-06-28 发布日期:2025-08-18
基金资助:
国家自然科学基金(82003585); 国家自然科学基金(21971224); 河南省高校科技创新人才支持计划(24HASTIT069); 河南省研究生教育改革与质量提升工程项目(YJS2025AL106); 河南省科技攻关项目(242102230095); 河南省高校基础研究专项(23ZX009); 河南师范大学优秀科技创新团队(2022TD03)

Iron-Photocatalytic Decarboxylative Functionalization Based on Ligand-to-Metal Charge Transfer

Chenchen Zhang^a, Qingjie Ding^a, Qiyan Lv^b^,^c, Chunhua Ma^a^,^*(), Yuqin Jiang^a^,^*(), Bing Yu^b^,^*()

^a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
^b College of Chemistry, Zhengzhou University, Zhengzhou 450001
^c National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037

Received:2025-05-22 Revised:2025-06-28 Published:2025-08-18
Contact: *E-mail: 2016007@htu.edu.cn; jiangyuqin@htu.edu.cn; bingyu@zzu.edu.cn
Supported by:
National Natural Science Foundation of China(82003585); National Natural Science Foundation of China(21971224); Program for Science & Technology Innovation Talents in Universities of Henan Province(24HASTIT069); Postgraduate Education Reform and Quality Improvement Project of Henan Province(YJS2025AL106); Key Science and Technology Project of Henan Province(242102230095); Special Project for Fundamental Research in University of Henan Province(23ZX009); Technical Innovation Team of Henan Normal University(2022TD03)

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摘要/Abstract

光催化羧酸的脱羧反应由于操作简便、条件温和, 近来引起了大量关注. 其中, 基于过渡金属配合物“配体-金属电荷转移”的光催化脱羧反应是一种有效的策略. 由于铁元素具有天然丰度高和毒性低的特点, 铁配合物参与的光催化脱羧反应在近年来得到迅速发展. 总结了近两年光诱导铁催化羧酸脱羧官能团化反应的研究进展, 旨在为开发新的方法奠定基础.

关键词: 羧酸, 脱羧, 光催化, 铁, 配体-金属电荷转移, 官能团化

Decarboxylation functionalization reactions of carboxylic acids via photocatalysis have garnered significant attention recently due to their operational simplicity and mild reaction conditions. Among these, photocatalytic decar- boxylation reactions based on transition metal complexes, particularly those involving ligand-to-metal charge transfer, represent an effective strategy. Due to the natural abundance and low toxicity of the iron element, photocatalytic decar- boxylation reactions involving iron complexes have gained huge attention. This review summarizes the recent advances in the field of light-induced iron-catalyzed decarboxylation functionalization reactions over the past two years, aiming to establish a foundation for the development of new methodologies.

Key words: carboxylic acid, decarboxylation, photocatalytic, iron, ligand-to-metal charge transfer, functionalization

引用此文

张晨晨, 丁清杰, 吕琪妍, 马春华, 姜玉钦, 於兵. 基于配体-金属电荷转移的铁催化光致脱羧官能团化反应[J]. 有机化学, 2025, 45(10): 3517-3533.

Chenchen Zhang, Qingjie Ding, Qiyan Lv, Chunhua Ma, Yuqin Jiang, Bing Yu. Iron-Photocatalytic Decarboxylative Functionalization Based on Ligand-to-Metal Charge Transfer[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3517-3533.

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图/表 16

图式1. 配体-金属电荷转移(LMCT)的过程

Scheme 1. Process of ligand-to-metal charge transfer (LMCT)

图式2. 铁(III)羧酸配合物中LMCT反应的基本原理

Scheme 2. Fundamental principles of LMCT reactions in iron(III) carboxylate complexes

图式3. 分子氧介导的光驱动铁催化羧酸脱羧氧化反应

Scheme 3. Molecular oxygen-mediated iron-photocatalyzed decarboxylative oxidation of carboxylic acids

图式4. 基于光驱动铁催化/TEMPO氧化体系的羧酸脱羧氧化反应

Scheme 4. Iron-photocatalysis/TEMPO oxidation system for decarboxylation oxidation of carboxylic acids

图式5. 光驱动铁催化的羧酸脱羧氢化反应

Scheme 5. Iron-photocatalytic decarboxylative hydrogenation of carboxylic acids

图式6. 基于光驱动铁催化羧酸脱羧的烯烃氢化氟烷基化反应

Scheme 6. Hydrofluoroalkylation of olefins via iron-photocatalytic decarboxylation of carboxylic acids

图式7. 光驱动铁催化的羧酸脱羧氟烷基化

Scheme 7. Iron-photocatalytic decarboxylative fluorination of carboxylic acids

图式8. 光驱动铁催化的羧酸脱羧卤化

Scheme 8. Iron-photocatalytic decarboxylative halogenation of carboxylic acids

图式9. 光驱动铁催化的羧酸脱羧叠氮化

Scheme 9. Iron-photocatalytic decarboxylative azidation of carboxylic acids

图式10. 光驱动铁铜双金属催化的羧酸脱羧胺化

Scheme 10. Photo-driven iron-copper bimetallic catalysis in the decarboxylative amination of carboxylic acids

图式11. 光驱动铁催化羧酸脱羧还原胺化反应

Scheme 11. Iron-photocatalytic decarboxylation/reductive amination of carboxylic acids

图式12. 光驱动铁催化的羧酸脱羧烯基化

Scheme 12. Iron-photocatalytic decarboxylative alkenylation of carboxylic acids

图式13. 光驱动铁催化的羧酸脱羧炔基化

Scheme 13. Iron-photocatalytic decarboxylative alkynylation of carboxylic acids

图式14. 光驱动铁催化羧酸的脱羧苯甲酰化

Scheme 14. Iron-photocatalytic decarboxylative benzoylation of carboxylic acids

图式15. 光驱动铁催化羧酸的脱羧硫醇化

Scheme 15. Iron-photocatalytic decarboxylative thiolation of carboxylic acids

图式16. 光诱导铁催化的羧酸脱羧磺酰化

Scheme 16. Iron-photocatalytic decarboxylative sulfonation of carboxylic acids

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基于配体-金属电荷转移的铁催化光致脱羧官能团化反应

Iron-Photocatalytic Decarboxylative Functionalization Based on Ligand-to-Metal Charge Transfer

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