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Synthesis 2023; 55(18): 2860-2872
DOI: 10.1055/a-2044-2140
DOI: 10.1055/a-2044-2140
short review
Special Issue Electrochemical Organic Synthesis
Photoelectrochemical Cerium Catalysis via Ligand-to-Metal Charge Transfer: A Rising Frontier in Sustainable Organic Synthesis
We greatly appreciate the financial support from the National Natural Science Foundation of China (Nos. 22171154, 22201152), the Special Funds of Taishan Scholar Project (No. tsqn202211206), the Youth Innovative Talents Recruitment and Cultivation Program of Shandong Higher Education, the Natural Science Foundation of Shandong Province (Nos. ZR2020QB008, ZR2020QB114, ZR2022QE142, and ZR2022QB215), Jinan Science and Technology Bureau (No. 2021GXRC080). The project was also supported by the Excellent Teaching Team Training Plan Project of Qilu University of Technology (Shandong Academy of Sciences) (2022JXTD020) and the Cultivating Project of Qilu University of Technology (Shandong Academy of Sciences) (2022PY002, 2022PX001, 2022PX003, 2022PY061).
Abstract
Photoelectrochemical cerium catalysis is an emerging and rapidly developing strategy in organic synthetic. A sustainable platform is being constructed by combining the concerted energy transfer from light and electricity to cerium with the ligand-to-metal charge transfer of excited state CeIV species. With this powerful strategy, hard to oxidized substrates can be activated under mild conditions, contributing to broad functional group compatibility. Such as, carboxylic acids, alcohols, and the Cl anion can deliver the corresponding radicals via formal single electron transfer (SET) with a low oxidation potential. Further cooperation with other synthetic strategies, including alkoxy radical promoted hydrogen atom transfer (HAT) and β-scission, leads to the functionalization of inert C(sp 3)–H, Si–H, and C–C bonds via a mild radical pathway. In this review, recent advances in photoelectrochemical cerium catalysis are described. More importantly, as this field features some unique advantages, but is rarely explored, we hope chemists will pay more attention to this catalytic system.
1 Introduction
2 Activation of Carboxylic Acids
3 Activation of Alcohols
3.1 Alkoxy Radical Involved Hydrogen Atom Transfer
3.2 Alkoxy Radical Promoted β-Scission
4 Formal Single-Electron Oxidation of Cl Anion
5 Conclusions and Outlook
Key words
Ce catalysis - photoelectrochemistry - CeIII/CeIV redox pair - photoinduced LMCT - single electron transferPublication History
Received: 18 January 2023
Accepted after revision: 28 February 2023
Accepted Manuscript online:
28 February 2023
Article published online:
06 April 2023
© 2023. Thieme. All rights reserved
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