Recent advances in photoredox catalytic transformations by using continuous-flow technology

doi:10.1016/S1872-2067(23)64447-X

Chinese Journal of Catalysis ›› 2023, Vol. 50: 175-194.DOI: 10.1016/S1872-2067(23)64447-X

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Recent advances in photoredox catalytic transformations by using continuous-flow technology

Xin Yuan^a, Hai-Bin Fan^a, Jie Liu^a, Long-Zhou Qin^a, Jian Wang^a, Xiu Duan^a, Jiang-Kai Qiu^a^,^b^,^*(), Kai Guo^a^,^b^,^*()

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu, China
^bState Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 211800, Jiangsu, China

Received:2023-03-15 Accepted:2023-05-03 Online:2023-07-18 Published:2023-07-25
Contact: *E-mail: qiujiangkai@njtech.edu.cn (J.-K Qiu), guok@njtech.edu.cn (K. Guo).
About author:Jiang-Kai Qiu (College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University) obtained his Ph.D. degree from Nanjing Tech University in 2016. He studied as an exchanged Ph.D. student in Jiangsu Normal University and Texas Tech University (US) in the lab of Prof. Shu-Jiang Tu and Guigen Li from 2013 to 2016. In 2017, he returned to Nanjing Tech University and joined Prof. Kai Guo's group to begin his research work and was promoted as a professor in 2022. His research interests focus on microflow-based green and sustainable technology.
Kai Guo (College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University) obtained his B.S. degree from Nanjing University in 2004, and Ph.D. degree from the Department of Chemistry at the University of Sheffield (UK) in 2008. Subsequently, he worked as the project manager at AF Chempharm Co. Ltd. (2008‒2009). After that, he began his postdoctoral study in the University of Sheffield (2009‒2010). In 2010, he started his independent research career at Nanjing Tech University as a professor. Currently, his research interests mainly focus on microflow technology and bio-based materials. He received the Second Prize of National Technology Invention Awards (2017), Feng Xinde Polymer Prizer (2017), International Award for Outstanding Young Chemical Engineer (2021), etc. He has published more than 200 peer-reviewed papers in Prog Polym. Sci., Appl. Catal. B, Angew. Chem. Int. Ed., Nat. Commun., Chem. Eng. J. etc.
Supported by:
National Natural Science Foundation of China(21702103);National Natural Science Foundation of China(21522604);Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture(XTD2203);Natural Science Research Projects of Jiangsu Higher Education(19KJB150027);Jiangsu Funding Program for Excellent Postdoctoral Talent(2022ZB389)

Abstract

Abstract:

Photoredox catalysis is regarded as an economically appealing method for highly efficient and sustainable chemical syntheses. Nevertheless, numerous recent studies have revealed several unresolved disadvantages; for example, based on the Bouguer-Lambert-Beer law, the short propagation distance of photons in traditional batch reactors hampers the scalability of photocatalytic reactions. The introduction of continuous-flow technology for photochemical synthesis has resolved several of these problems. The use of photochemistry in microreactors has resulted in various transformations. Superior mixing ability, more effective heat transfer, and the easier magnification of continuous-flow chemical reactions are key to its success. Continuous-flow technology has allowed the optimization of several different types of conversion. Photoredox catalysts are effective under various reaction conditions because of their single-electron transfer properties. Common photocatalysts include transition metal complexes containing ruthenium, iridium, copper, iron, or manganese; organic photocatalysts; and heterogeneous photocatalysts. This review covers the types of photocatalysts that have recently been used in continuous-flow photochemistry.

Key words: Photoredox catalysis, Continuous-flow technology, Transition metal photosensitizer, Organic photocatalyst, Heterogeneous photocatalyst

Xin Yuan, Hai-Bin Fan, Jie Liu, Long-Zhou Qin, Jian Wang, Xiu Duan, Jiang-Kai Qiu, Kai Guo. Recent advances in photoredox catalytic transformations by using continuous-flow technology[J]. Chinese Journal of Catalysis, 2023, 50: 175-194.

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Figures/Tables 55

Fig. 1. Photochemistry and microflow technology. (a) Photoredox catalysis; (b) The Bouguer-Lambert-Beer law; (c) Typical light-continuous-flow arrangement.

Fig. 2. Continuous-flow direct α-arylation of N,N-dialkylhydrazones.

Fig. 3. Photocatalytic radical-induced heterocycle migration.

Fig. 4. Schematic of the continuous-flow platform with a gas-liquid photoreactor.

Fig. 5. Continuous-flow photoredox transfer hydrogenation.

Fig. 6. Photocatalytic N-heterocycle formation.

Fig. 7. Monofluoroalkenylation of gem-difluoroalkenes with tetrahydrofuran (THF) in continuous flow.

Fig. 8. Trifluoromethylation/cyclization of 1,7-enynes under continuous flow conditions.

Fig. 9. Visible light-induced remote heteroaryl migration.

Fig. 10. Visible-light-induced chlorodifluoroacetic anhydride (CDFAA) for cyanoalkylacylation of azidyl homoallylic alcohols.

Fig. 11. Carbonylative alkene hydroacylation with alkyl halides.

Fig. 12. Trifluoromethylation and perfluoroalkylation with continuous-flow conditions.

Fig. 13. Visible light-mediated trifluoromethylation using CF3I gas.

Fig. 14. Continuous photo-flow hydrodifluoroalkylation.

Fig. 15. Hydrodifluoroalkylation of alkenes in a flow microreactor.

Fig. 16. Visible light decarboxylative functionalization of α-amino acid derivatives.

Fig. 17. Visible light-driven transformation of nitroalkanes to nitriles in a continuous-flow system.

Fig. 18. Manganese-catalyzed C-H arylation with continuous flow technology.

Fig. 19. Visible light-induced nickel Negishi reactions.

Fig. 20. S-functionalization of Cys-containing peptides in flow.

Fig. 21. Kumada-Corriu cross-coupling transformations in flow.

Fig. 22. Dual photoredox/nickel-catalyzed transformation.

Fig. 23. Iridium-nickel-catalyzed decarboxylative arylation.

Fig. 24. Iridium-nickel dual catalyzed strategy cross-coupling.

Fig. 25. Dual catalytic photoredox cross-electrophile coupling process.

Fig. 26. Nickel/photoredox N-(tert-butoxycarbonyl) (N-Boc) hydrazine coupling in continuous flow.

Fig. 27. Synthesis of useful phosphinamides, phosphonamides, and phosphoramides via dual copper and photoredox catalysis.

Fig. 28. Copper-catalyzed 1,4-cyanoalkylarylation.

Fig. 29. Catalytic generation of acyloxyphosphonium ions via photoredox catalysis.

Fig. 30. C-2 acylation of indoles catalyzed by dual Ir/Pd complexes.

Fig. 31. Photoredox C-N coupling between pyrrolidine and 4-bromobenzotrifluoride.

Fig. 32. Photoredox and nickel-catalyzed C-N cross-coupling process.

Fig. 33. C(sp3)-H alkylation catalyzed by TBADT.

Fig. 34. Decatungstate photocatalytic amination in flow.

Fig. 35. C-C bond formation mediated by TBADT catalyst in flow.

Fig. 36. Organic solvent nanofiltration (OSN) for in-line TBADT recovery in acetonitrile.

Fig. 37. Photoredox-catalyzed synthesis of α-amino acids.

Fig. 38. β-selective hydrocarboxylation of styrenes via para-terphenyl.

Fig. 39. Synthesis of semi-fluorinated poly(meth)acrylates via the photoredox organocatalyst phenothiazine core.

Fig. 40. Photochemical approaches toward bioactive amines/amino alcohols.

Fig. 41. Radical couplings with methyl vinyl ketone in a continuous-flow process.

Fig. 42. Large-scale photoredox Minisci reaction.

Fig. 43. Hydrogen-evolving cross-coupling of heteroarenes in the stop-flow microtubing (SFMT) reactor.

Fig. 44. Aliphatic alcohol-mediated Minisci-type reaction.

Fig. 45. Direct arylation of furan with a diazonium salt.

Fig. 46. Aerobic oxygenation of phenols by methylene blue in flow.

Fig. 47. C-H functionalization with 2,2′-bithiophene derivatives as photocatalyst.

Fig. 48. 18F-difluoromethylation of acyclovir.

Fig. 49. Photochemical tri- and difluoromethylation/cyclization strategy.

Fig. 50. Preparation of α-aminoamide derivatives.

Fig. 51. A photochemical [2+2] cycloaddition from aryl enamides.

Fig. 52. Combination of photocatalysis and immobilized enzyme catalysis for the synthesis of 2-phenylbenzothiazole (2-PBZ).

Fig. 53. Dichloromethyl radical addition to enones.

Fig. 54. Heterogeneous photocatalytic dimerization with K-intercalated carbon nitride (CN-K).

Fig. 55. C-H azolation of arenes with heterogeneous carbon nitride.

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Recent advances in photoredox catalytic transformations by using continuous-flow technology

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