Photoelectrochemical Cerium Catalysis via Ligand-to-Metal Charge Transfer: A Rising Frontier in Sustainable Organic Synthesis

Yuying Wang; Siyuan Liu; Jiangsheng Han; Ling Wang; Jianbin Chen

doi:10.1055/a-2044-2140

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2860-2872
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

Authors

Yuying Wang‡

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
Siyuan Liu‡

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
Jiangsheng Han

^bShanDongWeGo Pharmaceutical CO., LTD, Weihai 264414, P. R. of China
Ling Wang

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China
Jianbin Chen∗

^aShandong Provincial Key Laboratory of Molecular Engineering, School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, P. R. of China

Abstract

All articles of this category

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 Ce^IV 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 - Ce^III/Ce^IV redox pair - photoinduced LMCT - single electron transfer

Full Text

References

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