Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2019 Jun 15

PMID 31195644

Citations 17

Authors

Rik H Verschueren

Wim M De Borggraeve

Affiliations

Soon will be listed here.

Abstract

This review provides an overview of synthetic transformations that have been performed by both electro- and photoredox catalysis. Both toolboxes are evaluated and compared in their ability to enable said transformations. Analogies and distinctions are formulated to obtain a better understanding in both research areas. This knowledge can be used to conceptualize new methodological strategies for either of both approaches starting from the other. It was attempted to extract key components that can be used as guidelines to refine, complement and innovate these two disciplines of organic synthesis.

Citing Articles

Photocatalytic systems: reactions, mechanism, and applications.

Mohamadpour F, Amani A RSC Adv. 2024; 14(29):20609-20645.

PMID: 38952944 PMC: 11215501. DOI: 10.1039/d4ra03259d.

Paired Electrolysis Enables Reductive Heck Coupling of Unactivated (Hetero)Aryl Halides and Alkenes.

Lai Y, Milner P Angew Chem Int Ed Engl. 2024; 63(38):e202408834.

PMID: 38900083 PMC: 11427156. DOI: 10.1002/anie.202408834.

Electroreductive Radical Borylation of Unactivated (Hetero)Aryl Chlorides Without Light by Using Cumulene-Based Redox Mediators.

Lai Y, Halder A, Kim J, Hicks T, Milner P Angew Chem Int Ed Engl. 2023; 62(40):e202310246.

PMID: 37559156 PMC: 10529720. DOI: 10.1002/anie.202310246.

Acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst employed for the radical Michael-Mannich cyclocondensation of imines.

Mohamadpour F Front Chem. 2022; 10:1015330.

PMID: 36300032 PMC: 9590109. DOI: 10.3389/fchem.2022.1015330.

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer.

Mohamadpour F Front Chem. 2022; 10:934781.

PMID: 35923256 PMC: 9339953. DOI: 10.3389/fchem.2022.934781.

References

Wang Y, Gulevich A, Gevorgyan V . General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes. Chemistry. 2013; 19(47):15836-40. PMC: 3855880. DOI: 10.1002/chem.201303511. View

Schmidt A, Reddy K, Knolker H . Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev. 2012; 112(6):3193-328. DOI: 10.1021/cr200447s. View

Miller D, Choi G, Orbe H, Knowles R . Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer. J Am Chem Soc. 2015; 137(42):13492-5. PMC: 4629195. DOI: 10.1021/jacs.5b09671. View

Lin J, Song R, Hu M, Li J . Recent Advances in the Intermolecular Oxidative Difunctionalization of Alkenes. Chem Rec. 2018; 19(2-3):440-451. DOI: 10.1002/tcr.201800053. View

Cismesia M, Yoon T . Characterizing Chain Processes in Visible Light Photoredox Catalysis. Chem Sci. 2015; 6(10):5426-5434. PMC: 4676763. DOI: 10.1039/C5SC02185E. View

Shiri M . Indoles in multicomponent processes (MCPs). Chem Rev. 2012; 112(6):3508-49. DOI: 10.1021/cr2003954. View

Pletcher D, Green R, Brown R . Flow Electrolysis Cells for the Synthetic Organic Chemistry Laboratory. Chem Rev. 2017; 118(9):4573-4591. DOI: 10.1021/acs.chemrev.7b00360. View

Wiebe A, Gieshoff T, Mohle S, Rodrigo E, Zirbes M, Waldvogel S . Electrifying Organic Synthesis. Angew Chem Int Ed Engl. 2018; 57(20):5594-5619. PMC: 5969240. DOI: 10.1002/anie.201711060. View

Girard S, Knauber T, Li C . The cross-dehydrogenative coupling of C(sp3)-H bonds: a versatile strategy for C-C bond formations. Angew Chem Int Ed Engl. 2013; 53(1):74-100. DOI: 10.1002/anie.201304268. View

10.

Yang Q, Zhang L, Ye C, Luo S, Wu L, Tung C . Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis. Angew Chem Int Ed Engl. 2017; 56(13):3694-3698. DOI: 10.1002/anie.201700572. View

11.

Shen C, Zhang P, Sun Q, Bai S, Hor T, Liu X . Recent advances in C-S bond formation via C-H bond functionalization and decarboxylation. Chem Soc Rev. 2014; 44(1):291-314. DOI: 10.1039/c4cs00239c. View

12.

Beaupre S, Boudreault P, Leclerc M . Solar-energy production and energy-efficient lighting: photovoltaic devices and white-light-emitting diodes using poly(2,7-fluorene), poly(2,7-carbazole), and poly(2,7-dibenzosilole) derivatives. Adv Mater. 2010; 22(8):E6-E27. DOI: 10.1002/adma.200903484. View

13.

Fukuzumi S, Kotani H, Ohkubo K, Ogo S, Tkachenko N, Lemmetyinen H . Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center. J Am Chem Soc. 2004; 126(6):1600-1. DOI: 10.1021/ja038656q. View

14.

Trend R, Ramtohul Y, Ferreira E, Stoltz B . Palladium-catalyzed oxidative wacker cyclizations in nonpolar organic solvents with molecular oxygen: a stepping stone to asymmetric aerobic cyclizations. Angew Chem Int Ed Engl. 2003; 42(25):2892-5. DOI: 10.1002/anie.200351196. View

15.

Beck J, Chou S . The structural diversity of phthalides from the Apiaceae. J Nat Prod. 2007; 70(5):891-900. DOI: 10.1021/np0605586. View

16.

Yan M, Kawamata Y, Baran P . Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance. Chem Rev. 2017; 117(21):13230-13319. PMC: 5786875. DOI: 10.1021/acs.chemrev.7b00397. View

17.

Corsello M, Kim J, Garg N . Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies. Chem Sci. 2017; 8(9):5836-5844. PMC: 5618777. DOI: 10.1039/c7sc01248a. View

18.

Hering T, Slanina T, Hancock A, Wille U, Konig B . Visible light photooxidation of nitrate: the dawn of a nocturnal radical. Chem Commun (Camb). 2015; 51(30):6568-71. DOI: 10.1039/c5cc01580d. View

19.

Maity S, Zheng N . A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles. Angew Chem Int Ed Engl. 2012; 51(38):9562-6. PMC: 3522995. DOI: 10.1002/anie.201205137. View

20.

Su Y, Straathof N, Hessel V, Noel T . Photochemical transformations accelerated in continuous-flow reactors: basic concepts and applications. Chemistry. 2014; 20(34):10562-89. DOI: 10.1002/chem.201400283. View