光催化CO2参与的σ键断裂羧基化反应研究进展

doi:10.6023/cjoc202206003

有机化学 ›› 2022, Vol. 42 ›› Issue (12): 4257-4274.DOI: 10.6023/cjoc202206003 上一篇下一篇

所属专题：自由基化学专辑

综述与进展

光催化CO₂参与的σ键断裂羧基化反应研究进展

窦谦^a^,^b, 汪太民^a^,^*(), 李嗣锋^a, 房丽晶^a^,^b, 翟宏斌^a^,^c, 程斌^a^,^*()

a 深圳职业技术学院海洋生物医药研究院/博士后创新实践基地广东深圳 518055
b 中国科学院深圳先进技术研究院生物医药与技术研究所广东深圳 518055
c 北京大学深圳研究生院肿瘤化学基因组学国家重点实验室广东深圳 518055

收稿日期:2022-06-02 修回日期:2022-07-13 发布日期:2022-08-10
通讯作者: 汪太民, 程斌
基金资助:
广东省教育厅产教融合创新平台(2021CJPT014); 广东省教育厅创新团队(2022KCXTD054); 深圳职业技术学院深圳市高端人才科研启动(6022310047k); 深圳市科技创新委员会(JSGG20201103153800002); 深圳市科技创新委员会(GJHZ20200731095412037); 深圳市科技创新委员会(JCYJ20200109141808025); 深圳职业技术学院博士后基金(6021330006K)

Recent Advances in Photocatalytic Carboxylation with CO₂ via σ-Bond Cleavage

Qian Dou^a^,^b, Taimin Wang^a(), Sifeng Li^a, Lijing Fang^a^,^b, Hongbin Zhai^a^,^c, Bin Cheng^a()

a Institute of Marine Biomedicine, Postdoctoral Innovation Practice Base, Shenzhen Polytechnic, Shenzhen, Guangdong 518055
b Institute of Biomedicine and Biotechnology, Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen, Guangdong 518055
c State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, Guangdong 518055

Received:2022-06-02 Revised:2022-07-13 Published:2022-08-10
Contact: Taimin Wang, Bin Cheng
Supported by:
Innovation Platform for the Integration of Production and Education of Guangdong Provincial Education Department(2021CJPT014); Innovation Team of Guangdong Education Department(2022KCXTD054); Scientific Research Startup Fund for Shenzhen High-Caliber Personnel of Shenzhen Polytechnic(6022310047k); Shenzhen Science and Technology Innovation Committee(JSGG20201103153800002); Shenzhen Science and Technology Innovation Committee(GJHZ20200731095412037); Shenzhen Science and Technology Innovation Committee(JCYJ20200109141808025); Post-doctoral Foundation Project of Shenzhen Polytechnic(6021330006K)

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摘要/Abstract

二氧化碳(CO₂)作为温室气体的主要成分之一, 也是目前最丰富的碳源之一. CO₂常常作为C1合成子, 通过构建C—C键合成羧酸类化合物. 过渡金属催化的发展为CO₂的转化和利用提供了有力的工具. 为了实现“双碳”战略目标, 结合有机化学领域的研究热点, 发展绿色、可持续的CO₂转化和利用技术具有重要意义. 近年来, 光催化合成技术的发展为CO₂的转化和利用提供了新的契机. 系统阐述了光催化下CO₂参与的C—H、C—O、C—N及C—X键的断键及羧基化反应.

关键词: 光催化, CO₂, σ键断裂, 羧基化

Carbon dioxide (CO₂), as the main components of greenhouse gases, is one of the most abundant carbon sources at present. In organic chemistry, CO₂ is often used as C1 synthon to synthesize carboxylic acids by constructing C—C bond. Transition metal catalysis has developed as a powerful tool for the conversion and utilization of CO₂. In order to achieve the strategic goal of “double carbon”, it is of great significance to develop green and sustainable CO₂ conversion and utilization technology combined with contemporary hot topics in the field of organic chemistry. In recent years, the development of photocatalytic synthesis technology provied a new opportunity for the conversion and utilization of CO₂. The bond breaking of C—H bond, C—O bond, C—N and C—X bond and carboxylation reactions with CO₂ by photocatalysis strategy were systematically described.

Key words: photocatalysis, CO₂, σ-bond cleavage, carboxylation

引用此文

窦谦, 汪太民, 李嗣锋, 房丽晶, 翟宏斌, 程斌. 光催化CO₂参与的σ键断裂羧基化反应研究进展[J]. 有机化学, 2022, 42(12): 4257-4274.

Qian Dou, Taimin Wang, Sifeng Li, Lijing Fang, Hongbin Zhai, Bin Cheng. Recent Advances in Photocatalytic Carboxylation with CO₂ via σ-Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4257-4274.

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图/表 22

图式1. 光驱动下CO2参与的邻烷基芳基酮C(sp3)—H键羧基化反应

Scheme 1. Light-driven C(sp3)—H bonds carboxylation of o?alkylphenyl ketones with CO2

图式2. 光/铜双催化下CO2参与的烯丙基C(sp3)—H键羧基化反应

Scheme 2. Light/copper dual catalyzed carboxylation of allylic C(sp3)—H bonds of alkenes with CO2

图式3. 光催化下CO2参与的胺类化合物的C(sp3)—H键羧基化反应

Scheme 3. Photocatalyzed C(sp3)—H bonds carboxylation of amines with CO2

图式4. 光/镍双催化下CO2参与的苄基C(sp3)—H键羧基化反应

Scheme 4. Light/nickel dual catalyzed carboxylation of benzyl C(sp3)—H bonds with CO2

图式5. 有机光敏剂催化下CO2参与的苄基C(sp3)—H键羧基化反应

Scheme 5. Organic photosensitizer catalyzed carboxylation of benzyl C(sp3)—H bonds with CO2

图式6. 光/镍双催化下CO2参与的烷基溴化物的远程C(sp3)—H键羧基化反应

Scheme 6. Light/nickel dual catalyzed remote C(sp3)—H bonds carboxylation of alkyl bromides with CO2

图式7. 可见光催化的未活化烯烃与CO2的远程C(sp3)—H键羧基化反应

Scheme 7. Visible-light photoredox-catalyzed remote C(sp3)—H bonds carboxylation of unactivated alkenes with CO2

图式8. 可见光催化下CO2参与的芳基C—H键羧基化反应

Scheme 8. Visible-light photoredox catalyzed aryl C—H bonds carboxylation with CO2

图式9. 有机光敏剂催化CO2参与的芳基C—H键羧基化反应

Scheme 9. Organic photosensitizer catalyzed aryl C—H bonds carboxylation with CO2

图式10. 可见光/镍双催化下CO2参与的芳基C—O键羧基化反应

Scheme 10. Visible-light photoredox/nickel dual catalyzed aryl C—O bonds carboxylation with CO2

图式11. 可见光/钯双催化下CO2参与的芳基和烯基C—O键羧基化反应

Scheme 11. Visible-light photoredox/palladium dual catalyzed aryl and alkenyl C—O bonds carboxylation with CO2

图式12. 可见光/钯双催化下CO2参与的芳基C—O键羧基化反应

Scheme 12. Visible-light photoredox/palladium dual catalyzed aryl C—O bonds carboxylation with CO2

图式13. 可见光/钯双催化下CO2参与的苄基C—O键羧基化反应

Scheme 13. Visible-light photoredox/palladium dual catalyzed benzyl C—O bonds carboxylation with CO2

图式14. 有机光敏剂催化下CO2参与的苄基C—O键羧基化反应

Scheme 14. Organic photosensitizer catalyzed benzyl C—O bonds carboxylation with CO2

图式15. 可见光催化下CO2参与的苄醇C—O键羧基化反应

Scheme 15. Visible-light photoredox catalyzed C—O bonds carboxylation of benzyl alcohol with CO2

图式16. 可见光与镍协同催化下CO2参与的烯丙醇C—O键羧基化反应

Scheme 16. Visible-light photoredox/nickel dual catalyzed allylic C—O bonds carboxylation with CO2

图式17. 可见光催化下CO2参与的季铵盐C—N键羧基化反应

Scheme 17. Visible-light photoredox catalyzed C—N bonds carboxylation of tetraalkyl ammonium salts with CO2

图式18. 可见光/钯双催化下CO2参与的芳基C—Br/Cl键羧基化反应

Scheme 18. Visible-light photoredox/palladium dual catalyzed aryl C—Br/Cl bonds carboxylation with CO2

图式19. 可见光/镍双催化下CO2参与的芳基和烷基C—Br键羧基化反应

Scheme 19. Visible-light photoredox/nickel dual catalyzed aryl and alkyl C—Br bonds carboxylation with CO2

图式20. 有机光敏剂催化下CO2参与的苄基C—Br/Cl键羧基化反应

Scheme 20. Organic photosensitizer catalyzed benzyl C—X bonds carboxylation with CO2

图式21. 可见光/钯双催化下CO2参与的烯基C—F键羧基化反应

Scheme 21. Visible-light photoredox/palladium dual catalyzed alkenyl C—F bonds carboxylation with CO2

图式22. 可见光催化下CO2参与的烷基C—F键羧基化反应

Scheme 22. Visible-light photoredox catalyzed alkyl C—F bonds carboxylation with CO2

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光催化CO₂参与的σ键断裂羧基化反应研究进展

Recent Advances in Photocatalytic Carboxylation with CO₂ via σ-Bond Cleavage

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