Recent Development of Photoinduced Iron-Catalysis in Organic Synthesis

doi:10.6023/cjoc202209001

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1386-1415.DOI: 10.6023/cjoc202209001 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 41

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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