光诱导铁催化在有机合成中的应用研究进展

doi:10.6023/cjoc202209001

有机化学 ›› 2023, Vol. 43 ›› Issue (4): 1386-1415.DOI: 10.6023/cjoc202209001 上一篇下一篇

综述与进展

光诱导铁催化在有机合成中的应用研究进展

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

a 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
b 深圳职业技术学院/海洋生物医药研究院广东深圳 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:2022-09-01 修回日期:2022-10-15 发布日期:2022-11-15
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(6021210004P); 广东省教育厅创新团队(2021KCXTD069); 深圳职业技术学院深圳市高端人才科研启动项目(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 Development of Photoinduced Iron-Catalysis in Organic Synthesis

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

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

Received:2022-09-01 Revised:2022-10-15 Published:2022-11-15
Contact: Taimin Wang, Bin Cheng
Supported by:
Marine Medicine Innovation Platform for the Integration of Production and Education of Guangdong Provincial Education Department(6021210004P); Innovation Team of Guangdong Education Department(2021KCXTD069); Scientific Research Startup Fund for Shenzhen High-Caliber Personnel of Shenzhen Polytechnic(6022310047k); Shenzhen Science and Technology Innovation Committee(GJHZ20200731095412037); Shenzhen Science and Technology Innovation Committee(JCYJ20200109141808025); Post-doctoral Foundation Project of Shenzhen Polytechnic(6021330006K); Shenzhen Science and Technology Innovation Committee(JSGG- 20201103153800002)

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摘要/Abstract

近年来, 以过渡金属钌和铱络合物为代表的光催化剂的开发和应用为有机合成开启了新篇章, 这些过渡金属光催化剂参与的光催化反应为化学键的构筑和有机转化提供了温和高效的新策略. 为了丰富光催化剂的种类, 拓宽光催化体系的适用范围, 发展绿色可持续化学, 近年来一些廉价易得的过渡金属比如铜、铁等被相继开发用作光催化剂. 其中, 铁催化剂因其无毒、种类丰富, 并且具有独特的配体-金属电荷转移性质, 在光催化合成领域大放异彩. 依据反应类型对光诱导铁催化反应进行了综述, 主要包括C—H键官能团化反应、C—C键官能团化反应、烯烃双官能团化反应、交叉偶联反应、脱羧官能团化反应、选择性氧化和还原反应.

关键词: 光化学, 铁催化, 自由基, 绿色化学, 有机合成

In recent years, the development and application of transition metal ruthenium or iridium complexes based photocatalysts have opened up a new research field for organic synthesis, which provides mild and efficient strategies for the construction of chemical bonds and organic transformations. In order to enrich the types of photocatalysts, broaden the application scope of photocatalysis, and develop green and sustainable chemistry, some low-cost and easily available organometallic complexes with copper or iron were applied as photocatalysts recently. Iron-complexes feature non-toxicity, rich variety, and unique property of charge transfer from ligands to metals, which enable them show extraordinary capability in the field of photocatalytic synthesis. According to different reaction types, this review focuses on the recent development of photoinduced iron-catalysis in organic synthesis including C—H bond functionalization, C—C bond functionalization, bifunctionalization of alkenes, cross-coupling reaction, decarboxylative functionalization, selective oxidation and reduction.

Key words: photo-chemistry, iron-catalysis, radical, green-chemistry, organic synthesis

引用此文

窦谦, 汪太民, 房丽晶, 翟宏斌, 程斌. 光诱导铁催化在有机合成中的应用研究进展[J]. 有机化学, 2023, 43(4): 1386-1415.

Qian Dou, Taimin Wang, Lijing Fang, Hongbin Zhai, Bin Cheng. Recent Development of Photoinduced Iron-Catalysis in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1386-1415.

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图/表 41

图式1. 光诱导铁催化二芳基胺化合物分子内C(sp2)—H键的芳基化反应

Scheme 1. Photoinduced iron-catalyzed intramolecular arylation of C(sp2)—H bond of diarylamines

图式2. 可见光诱导铁催化的杂环化合物C(sp2)—H键的烷基化反应

Scheme 2. Visible light-induced iron-catalyzed alkylation of C(sp2)—H bonds of heterocyclic compounds

图式3. 可见光诱导铁催化的2-联芳基羧酸化合物的分子内芳基C—H键酯化反应

Scheme 3. Visible light-induced iron-catalyzed intramolecular esterification of aryl C—H bond of 2-biaryl carboxylic acids

图式4. 可见光诱导下铁催化1,4-萘醌的C(sp2)—H键亚磺酰亚胺化反应

Scheme 4. Visible-light-induced iron-catalyzed C(sp2)—H sulfimidization of 1,4-naphthoquinones

图式5. 可见光诱导下铁(III)卟啉催化的C(sp3)—H键胺化反应

Scheme 5. Visible light-induced Iron(III) porphyrin catalyzed C(sp3)—H bond amination

图式6. 可见光诱导铁催化的C(sp3)—H键酰胺化反应

Scheme 6. Visible light-induced iron-catalyzed C(sp3)—H bond amidation

图式7. 可见光诱导铁催化的1,3-二羰基化合物的C(sp3)—H键酰胺化反应

Scheme 7. Visible light-induced iron-catalyzed C(sp3)—H bond amidation of 1,3-dicarbonyls

图式8. 可见光诱导铁催化四氢呋喃和四氢噻吩的α-C(sp3)—H的胺化反应

Scheme 8. Visible light-induced iron-catalyzed α-C(sp3)—H bond amination of tetrahydrofuran and tetrahydrothiophene

图式9. 可见光诱导铁催化的C(sp3)—H的胺化和烷基化反应

Scheme 9. Visible light-induced iron-catalyzed C(sp3)—H bond amination and alkylation

图式10. 可见光诱导下铁催化的C(sp3)—H键烷基化反应

Scheme 10. Visible light-induced iron-catalyzed C(sp3)—H bond alkylation

图式11. 可见光诱导铁催化甲烷等气态烷烃的官能团化反应

Scheme 11. Visible light-induced iron-catalyzed functionalization of methane and other gaseous alkanes

图式12. 可见光诱导铁催化的C(sp3)—H的炔基化反应

Scheme 12. Visible light-induced iron-catalyzed C(sp3)—H bond alkynylation

图式13. 可见光诱导铁催化酮类化合物的α-C(sp3)—H的烷基化反应

Scheme 13. Visible light-induced iron-catalyzed α-C(sp3)—H bond alkylation of ketones

图式14. 可见光诱导铁催化酮类化合物的α-C(sp3)—H的甲基化反应

Scheme 14. Visible light-induced iron-catalyzed α-C(sp3)—H bond methylation of ketones

图式15. 可见光诱导铁催化醇的α-C—C键断裂并氧化为芳香羧酸反应

Scheme 15. Visible light-induced iron-catalyzed oxidative α-C—C bond cleavage of alcohols to aromatic acids with O2

图式16. 可见光诱导铁催化芳基化合物的氧化反应

Scheme 16. Visible light-induced iron-catalyzed oxidation of alkyl aromatics

图式17. 可见光诱导铁催化醇类化合物的C—C键断裂反应

Scheme 17. Visible light-induced iron-catalyzed C—C bond cleavage of alcohols

图式18. 可见光诱导铁催化醇类化合物的C—C键断裂烷基化反应

Scheme 18. Visible light-induced iron-catalyzed C—C bond cleavage and alkylation of alcohols

图式19. 可见光诱导铁催化环状醇类化合物的C—C键断裂胺基化反应

Scheme 19. Visible light-induced iron-catalyzed C—C bond cleavage and amination of unstrained cyclic alcohols

图式20. 可见光诱导铁催化环状醇类化合物的C—C键断裂溴化和碘化反应

Scheme 20. isible light-induced iron-catalyzed C—C bond cleavage and bromination and iodination of unstrained cyclic alcohols

图式21. 可见光诱导铁催化CO2参与的烯烃化合物的硫-羧基化反应

Scheme 21. Visible light-induced iron-catalyzed thiocarboxylation of alkenes with CO2

图式22. 可见光诱导铁催化烯烃化合物的甲基-芳基化反应

Scheme 22. Visible light-induced iron-catalyzed methylation-arylation of alkenes

图式23. 可见光诱导铁催化烯烃化合物的烷基化反应

Scheme 23. Visible light-induced iron-catalyzed alkylation of alkenes

图式24. 可见光诱导铁催化烯烃化合物的胺基硒化反应

Scheme 24. Visible light-induced iron-catalyzed aminoselenation of alkenes

图式25. 可见光诱导铁催化非活化烯烃化合物的碳-卤化反应

Scheme 25. Visible light-induced iron-catalyzed carbon-halogenation of unactivated alkenes

图式26. 可见光诱导铁催化烯烃化合物的硅氢化反应

Scheme 26. Visible light-induced iron-catalyzed hydrosilylatio of alkenes

图式27. 流动相中可见光诱导铁催化的C(sp2)—C(sp3) Kumada交叉偶联反应

Scheme 27. Visible light-induced iron-catalyzed C(sp2)—C(sp3) Kumada cross-coupling in flow

图式28. 可见光诱导铁催化的芳基C—N键交叉偶联反应

Scheme 28. Visible light-induced iron-catalyzed aryl C—N bond cross-coupling

图式29. 可见光诱导铁催化的酰基C—N键交叉偶联反应

Scheme 29. Visible light-induced iron-catalyzed acyl C—N bond cross-coupling

图式30. 可见光诱导铁催化C(sp3)—C(sp3)键的不对称交叉偶联反应

Scheme 30. Visible light-induced iron-catalyzed asymmetric C(sp3)—C(sp3) bond cross-coupling reaction

图式31. 可见光诱导铁催化的烷基羧酸的脱羧氟化反应

Scheme 31. Visible light-induced iron-catalyzed decarboxylative fluorination of alkyl carboxylic acids

图式32. 可见光诱导铁催化的烷基羧酸的脱羧氧化反应

Scheme 32. Visible light-induced iron-catalyzed decarboxylative oxidation of alkyl carboxylic acids

图式33. 可见光诱导铁催化苄基化合物和烯基卤代物的选择性氧化反应

Scheme 33. Visible light-induced iron-catalyzed selective aerobic oxidation of benzyl compounds and vinyl halides

图式34. 可见光诱导铁催化聚苯乙烯的选择性氧化降解反应

Scheme 34. Visible light-induced iron-catalyzed oxidative degradation of polystyrene

图式35. 可见光诱导铁催化酮和醛类化合物的选择性氢化还原反应

Scheme 35. Visible light-induced iron-catalyzed selective hydrogenation and reduction of ketones and aldehydes

图式36. 可见光诱导铁催化酯类化合物的选择性氢化还原反应

Scheme 36. Visible light-induced iron-catalyzed selective hydrogenation and reduction of esters

图式37. 可见光诱导铁催化酰胺类化合物的选择性氢化还原反应

Scheme 37. Visible light-induced iron-catalyzed selective hydrogenation and reduction of amides

图式38. 可见光诱导铁催化亚胺类化合物的选择性氢化还原反应

Scheme 38. Visible light-induced iron-catalyzed selective hydrogenation and reduction of imines

图式39. 可见光诱导铁催化环醚和缩醛的开环卤化反应

Scheme 39. Visible light-induced iron-catalyzed ring opening and halogenation of cyclic ethers and acetals

图式40. 可见光诱导铁催化末端芳基乙烯和亲核二烯烃的[4＋2]环加成反应

Scheme 40. Visible light-induced iron-catalyzed [4＋2] cycloaddition of terminal styrenes and nucleophilic dienes

图式41. 可见光诱导铁催化氢硅烷的炔基化反应

Scheme 41. Visible light-induced iron-catalyzed alkynylation of hydrosilanes

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光诱导铁催化在有机合成中的应用研究进展

Recent Development of Photoinduced Iron-Catalysis in Organic Synthesis

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