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Review
. 2023 May 19;88(10):6284-6293.
doi: 10.1021/acs.joc.2c00805. Epub 2022 Jun 14.

Visible-Light Photoredox Catalysis in Water

Camilla Russo  1 , Francesca Brunelli  2 , Gian Cesare Tron  2 , Mariateresa Giustiniano  1
Affiliations
Review

Visible-Light Photoredox Catalysis in Water

Camilla Russo et al. J Org Chem. .

Abstract

The use of water in organic synthesis draws attention to its green chemistry features and its unique ability to unveil unconventional reactivities. Herein, literature about the use of water as a reaction medium under visible-light photocatalytic conditions is summarized in order to highlight challenges and opportunities. Accordingly, this Synopsis has been divided into four different sections focused on (1) the unconventional role of water in photocatalytic reactions, (2) in-/on-water reactions, (3) water-soluble photocatalysts, and (4) photomicellar catalytic systems.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Chemoselective Photoreduction of Aldehydes in the Presence of Ketones
Scheme 2
Scheme 2. Light-Driven Reduction of Aldehydes and Aromatic Ketones
Scheme 3
Scheme 3. Photocatalytic Pinacol Coupling
Alternatively, [Ru(dmb)3]2+ was used as PC; dmb: tris(4,4′-dimethyl-2,2′-bipyridine)ruthenium(II).
Scheme 4
Scheme 4. Intramolecular Reductive Proton Transfer from Carbonyls to Alcohols
Scheme 5
Scheme 5. Iridium-Promoted Synthesis of Isoxazolidines
Scheme 6
Scheme 6. Deboronative Cyanation
Scheme 7
Scheme 7. Photocatalytic Cross-Coupling of α-Carbonyl Acetates with Styrenes
Scheme 8
Scheme 8. Radical Conjugate Addition of Nitrogen Heterocycles to Electron-Poor Alkenes
Scheme 9
Scheme 9. Chemoselective Synthesis of Hydro- and Dibromofluoromethylated Adducts
Scheme 10
Scheme 10. Direct Arylation of N-Heteroarenes with Aryldiazonium Tetrafluoroborate Salts
Scheme 11
Scheme 11. Catalytic Dehydrogenation of Cyclic Amines
Scheme 12
Scheme 12. Metal-Free Oxidative Radical Cyclization of N-Biarylglycin Esters
Scheme 13
Scheme 13. (a) C3–H Acylation of Quinoxaline-2(1H)-ones 41. (b) Synthesis of 1,2-Amino alcohols 43. (c) Epoxyacylation and Hydroacylation of Olefins 44 and 45
Figure 1
Figure 1
[Ir(dF(CF3)ppy)2(dtbbpy)]PF6 and its water-soluble analogue [Ir(dF(CF3)ppy)2(dNMe3bpy)]Cl3.
Scheme 14
Scheme 14. Trifluoromethylation of Unprotected Dipeptide 48 in Phosphate-Buffered Saline Solvent
Scheme 15
Scheme 15. Bromination and Iodination of 8-Aminoquinoline Amides in Water
Scheme 16
Scheme 16. Oxidation of Aromatic and Aliphatic Alcohols in Water
Scheme 17
Scheme 17. Oxidation of Alkenes 56 to Epoxides 57 in water
Scheme 18
Scheme 18. Photooxidation of Alcohols to Aldehydes and Carboxylic Acids
Scheme 19
Scheme 19. Oxidative Dehydrogenation of N-Heterocycles in a Biphasic System
Scheme 20
Scheme 20. Difunctionalization of Alkenes 61 and Sulfonylation of Enol Acetates 64 Promoted by PQS-[Ir]
Scheme 21
Scheme 21. Arylation of Heteroarenes and Enol Acetates and Synthesis of Sulfides and Selenides
Scheme 22
Scheme 22. Direct Arylations of Aryl Bromides in Water
Scheme 23
Scheme 23. One-Pot Synthesis of Pyridines
Scheme 24
Scheme 24. Photomicellar Catalytic Minisci C–H Functionalization of Heteroarenes
Scheme 25
Scheme 25. Chemodivergent Intramolecular C–H Arylation and N-Dealkylation of o-Chlorobenzamides 83
Scheme 26
Scheme 26. Photomicellar Catalytic Synthesis of Amides Starting from Isocyanides and Tertiary Aromatic Amines
See this image and copyright information in PMC

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