Recent Advances in Electro- or Photochemical Driven Transformations via Cleavage of the C–N Bond of Quaternary Ammonium Salts

Xiaohui Chen; Neng-Zhong Wang; Ya-Min Cheng; Xianqiang Kong; Zhong-Yan Cao

doi:10.1055/a-2020-8923

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2833-2842
DOI: 10.1055/a-2020-8923

short review

Special Issue Electrochemical Organic Synthesis

Recent Advances in Electro- or Photochemical Driven Transformations via Cleavage of the C–N Bond of Quaternary Ammonium Salts

Xiaohui Chen

^aSchool of Chemical Engineering and Materials, Changzhou Institute of Technology, No. 666 Liaohe Road, Changzhou 213032, P. R. of China

,

Neng-Zhong Wang

^bHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, P. R. of China

,

Ya-Min Cheng

^cCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China

,

Xianqiang Kong∗

^aSchool of Chemical Engineering and Materials, Changzhou Institute of Technology, No. 666 Liaohe Road, Changzhou 213032, P. R. of China

,

Zhong-Yan Cao∗

^cCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China

› Author Affiliations

Abstract

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Abstract

Selective functionalization via cleavage of the C–N bond of amines has proven to be challenging partly because of its relatively high bond dissociation energy, even though amines are abundant and readily available. To meet this challenge, many new transformations based on the pre-activation of the C–N bond before the cleavage have been developed. Among them, the conversion of amines into quaternary ammonium salts has certain advantages, such as easy preparation from primary, secondary, or tertiary amines, as well as stable storage and usage. Although transition metal catalysis has been frequently applied for developing new transformations via oxidative addition of the C–N bond of quaternary ammonium salts, recent studies have shown a new dimension by using green electro- or photochemical tools. In this short review, recent advances in electro-, photo-, or photoelectrochemical driven synthetic applications of quaternary ammonium salts have been summarized and discussed.

1 Introduction

2 Electrochemical Driven Transformations

3 Photochemical Driven Transformations

4 Photoelectrochemical Driven Transformations

5 Conclusion and Outlook

Key words

quaternary ammonium salts - synthetic transformation - C–N bond cleavage - amines - electrochemistry - photochemistry

Full Text

References

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