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Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Cite this: Chem. Rev. 2022, 122, 2, 2487–2649
Publication Date (Web):November 9, 2021
https://doi.org/10.1021/acs.chemrev.1c00384
Copyright © 2021 American Chemical Society

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    Abstract

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    Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do electrochemistry and photoredox catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) that enable bond formations not constrained by the rules of ionic or 2 electron (e) mechanisms. Instead, they enable 1e mechanisms capable of bypassing electronic or steric limitations and protecting group requirements, thus enabling synthetic chemists to disconnect molecules in new and different ways. However, while providing access to similar intermediates, electrochemistry and photoredox catalysis differ in several physical chemistry principles. Understanding those differences can be key to designing new transformations and forging new bond disconnections. This review aims to highlight these differences and similarities between electrochemistry and photoredox catalysis by comparing their underlying physical chemistry principles and describing their impact on electrochemical and photochemical methods.

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    46. Alexandra C. Sun Corey R. J. Stephenson Robert T. Kennedy . High-Throughput Photochemistry Using Droplet Microfluidics. , 131-143. https://doi.org/10.1021/bk-2022-1419.ch008
    47. Jonas Rein Song Lin Dipannita Kalyani Dan Lehnherr . High-Throughput Experimentation for Electrochemistry. , 167-187. https://doi.org/10.1021/bk-2022-1419.ch010
    48. Hongyan Zhou, Rundong Fan, Jingya Yang, Ximei Sun, Xiaojun Liu, Xi-Cun Wang. N,N-Diisopropylethylamine-Mediated Electrochemical Reduction of Azobenzenes in Dichloromethane. The Journal of Organic Chemistry 2022, 87 (21) , 14536-14543. https://doi.org/10.1021/acs.joc.2c01949
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    72. Luke V. Lutkus, Aaron Krytenberg, Jayce Taylor, Avik Bhattacharjee, Bret A. Steinkamp, Theresa M. McCormick. Simplification of the potassium ferrioxalate actinometer through carbon dioxide monitoring. Canadian Journal of Chemistry 2023, 101 (3) , 171-176. https://doi.org/10.1139/cjc-2022-0188
    73. Leonardo Rapisarda, Andrea Fermi, Paola Ceroni, Riccardo Giovanelli, Giulio Bertuzzi, Marco Bandini. Electrochemical C(sp 3 )–H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction. Chemical Communications 2023, 59 (18) , 2664-2667. https://doi.org/10.1039/D2CC06999G
    74. Linge Huai, Li Zhang, Zhentao Wang, Hao Wu, Yewen Fang. Cyclopropanation of N -vinylimides via a redox-neutral photocatalysed radical addition/anionic cyclisation process. Organic Chemistry Frontiers 2023, 10 (5) , 1245-1251. https://doi.org/10.1039/D2QO01892F
    75. Xiao Zhang, Qilin Yuan, Haoxiang Zhang, Zheng-Jia Shen, Lulu Zhao, Chao Yang, Lin Guo, Wujiong Xia. Electrochemical synthesis of oxazoles via a phosphine-mediated deoxygenative [3 + 2] cycloaddition of carboxylic acids. Green Chemistry 2023, 25 (4) , 1435-1441. https://doi.org/10.1039/D2GC04559A
    76. Yufeng Li, Lirong Wen, Weisi Guo. A guide to organic electroreduction using sacrificial anodes. Chemical Society Reviews 2023, 52 (4) , 1168-1188. https://doi.org/10.1039/D3CS00009E
    77. Yangjie Yi, Leitao Xu, Yuyang Liu, Mingfang Li, Lijuan Zhang, Jiao Ye, Aixi Hu. Solvent-dependence of KI Mediated Electrosynthesis of Imidazo[1,2-a]pyridines. Chemical Research in Chinese Universities 2023, 144 https://doi.org/10.1007/s40242-023-2323-y
    78. Yanxia Lv, Zhong-Wei Hou, Pinhua Li, Lei Wang. Paired electrochemical C–H bromination of (hetero)arenes with 2-bromoethan-1-ol. Organic Chemistry Frontiers 2023, 10 (4) , 990-995. https://doi.org/10.1039/D2QO01425D
    79. Hong Liu, Wan Lei, Yan Li, Yewen Fang. Diversified access to di- and trisubstituted allenes via nickel-catalysed reactions of 1,3-enynes with alkyl N -hydroxyphthalimide esters. Chemical Communications 2023, 59 (13) , 1825-1828. https://doi.org/10.1039/D2CC06544D
    80. Elena Bassan, Francesco Calogero, Yasi Dai, Angela Dellai, Alessandro Franceschinis, Emanuele Pinosa, Fabrizia Negri, Andrea Gualandi, Paola Ceroni, Pier Giorgio Cozzi. Meso ‐2‐MethoxyNaphthalenyl‐BODIPY as Efficient Organic Dye for Metallaphotoredox Catalysis. ChemCatChem 2023, 15 (3) https://doi.org/10.1002/cctc.202201380
    81. Yunlong Liu, Pengcheng Zhou, Yingli Xu, Zhiqi Yang, Dong Wang. Electrochemically driven [4+2] benzannulation: synthesis of polycyclic (hetero)aromatic compounds. Chemical Communications 2023, 59 (12) , 1681-1684. https://doi.org/10.1039/D2CC06552E
    82. Sylvain Oudeyer, Vincent Levacher, Hélène Beucher, Jean-François Brière. Recent Advances in Catalytic and Technology-Driven Radical Addition to N,N-Disubstituted Iminium Species. Molecules 2023, 28 (3) , 1071. https://doi.org/10.3390/molecules28031071
    83. Beibei Zhang, Junfei Luo, Yewen Fang. Access to functionalized alkynylcyclopropanes via reductive radical-polar crossover-based reactions of 1,3-enynes with alkyl radicals. Organic & Biomolecular Chemistry 2023, 21 (4) , 732-737. https://doi.org/10.1039/D2OB02155B
    84. Antonio Pulcinella, Stefano Bonciolini, Florian Lukas, Andrea Sorato, Timothy Noël. Photocatalytic Alkylation of C(sp 3 )−H Bonds Using Sulfonylhydrazones**. Angewandte Chemie 2023, 135 (3) https://doi.org/10.1002/ange.202215374
    85. Antonio Pulcinella, Stefano Bonciolini, Florian Lukas, Andrea Sorato, Timothy Noël. Photocatalytic Alkylation of C(sp 3 )−H Bonds Using Sulfonylhydrazones**. Angewandte Chemie International Edition 2023, 62 (3) https://doi.org/10.1002/anie.202215374
    86. Kingshuk Mahanty, Atreyee Halder, Suman De Sarkar. Synthesis of N ‐Sulfonyl Amidines and 1,3,4‐Oxadiazoles through Electrochemical Activation of DMF. Advanced Synthesis & Catalysis 2023, 365 (1) , 96-103. https://doi.org/10.1002/adsc.202201019
    87. Xichang Dong, Martin Klein, Siegfried R. Waldvogel, Bill Morandi. Kontrolle der Selektivität in Shuttle‐Heterodifunktionalisierungen: Elektrochemische Transfer‐Halothiolierung von Alkinen. Angewandte Chemie 2023, 135 (2) https://doi.org/10.1002/ange.202213630
    88. Xichang Dong, Martin Klein, Siegfried R. Waldvogel, Bill Morandi. Controlling Selectivity in Shuttle Hetero‐difunctionalization Reactions: Electrochemical Transfer Halo‐thiolation of Alkynes. Angewandte Chemie International Edition 2023, 62 (2) https://doi.org/10.1002/anie.202213630
    89. Patrick Enders, Michal Májek, Chiu Marco Lam, R. Daniel Little, Robert Francke. How to Harness Electrochemical Mediators for Photocatalysis – A Systematic Approach Using the Phenanthro[9,10‐ d ]imidazole Framework as a Test Case. ChemCatChem 2023, 15 (1) https://doi.org/10.1002/cctc.202200830
    90. Stephanie G. E. Amos, Franck Le Vaillant, Jerome Waser. Exploring Photoredox‐Catalyzed (Re)functionalizations with Core‐Modified Benziodoxolones. Helvetica Chimica Acta 2023, 106 (1) https://doi.org/10.1002/hlca.202200161
    91. Jiami Guo, Zi-An Shen, Xueting Zhou, Lei Dai, Yixin Lu. Light-induced phosphine-catalyzed asymmetric functionalization of benzylic C-H bonds. Science China Chemistry 2023, 66 (1) , 127-132. https://doi.org/10.1007/s11426-022-1406-y
    92. Kingshuk Mahanty, Suman Kumar Saha, Atreyee Halder, Suman De Sarkar. Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines. Chemical Communications 2023, 51 https://doi.org/10.1039/D3CC00231D
    93. Xue-Qi Zhou, Pei-Bo Chen, Qiang Xia, Ting-Kai Xiong, Xue-Jun Li, Ying-Ming Pan, Mu-Xue He, Ying Liang. Indirect electrochemical reductive cyclization of o -halophenylacrylamides mediated by phenanthrene. Organic Chemistry Frontiers 2023, 25 https://doi.org/10.1039/D3QO00280B
    94. Abing Duan, Fengjiao Xiao, Yu Lan, Linbin Niu. Mechanistic views and computational studies on transition-metal-catalyzed reductive coupling reactions. Chemical Society Reviews 2022, 51 (24) , 9986-10015. https://doi.org/10.1039/D2CS00371F
    95. Zuzana Burešová, Veronika Jandová, Milan Klikar, Monika Grygarová, Filip Bureš. Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling. Organic & Biomolecular Chemistry 2022, 20 (47) , 9378-9384. https://doi.org/10.1039/D2OB01836E
    96. Xinyu Chang, Xingyue Wen, Danheng Gao, Meng Luo, Pingping Teng, Zheng Zhu, Jianzhong Zhang, Kang Li, Nigel Copner, Xinghua Yang. Optoelectrode based on conductive fiber Fabry-Perot probe for simultaneous electrochemical and optical sensing. Measurement 2022, 205 , 112198. https://doi.org/10.1016/j.measurement.2022.112198
    97. Li Li, Kun Deng, Yajie Xing, Cheng Ma, Shao-Fei Ni, Zhaofeng Wang, Yong Huang. Synthesis of I(III)/S(VI) reagents and their reactivity in photochemical cycloaddition reactions with unsaturated bonds. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-34401-7
    98. Ze‐Le Chen, Yang Xie, Jun Xuan. Visible Light‐Mediated Cyclopropanation: Recent Progress. European Journal of Organic Chemistry 2022, 2022 (44) https://doi.org/10.1002/ejoc.202201066
    99. Sota Adachi, Genki Horiguchi, Hidehiro Kamiya, Yohei Okada. Photochemical Radical Cation Cycloadditions of Aryl Vinyl Ethers. European Journal of Organic Chemistry 2022, 2022 (44) https://doi.org/10.1002/ejoc.202201207
    100. Jens Lefarth, Alexander Haseloer, Lukas Kletsch, Axel Klein, Jörg Neudörfl, Axel G. Griesbeck. From energy to electron transfer photocatalysis (PenT → PET): oxidative cyclobutane cleavage alters the product composition. Chemical Communications 2022, 58 (93) , 12999-13002. https://doi.org/10.1039/D2CC04693H
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