State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, Shaanxi, China.
Chem Rev. 2021 Jan 13;121(1):485-505. doi: 10.1021/acs.chemrev.0c00335. Epub 2020 Oct 5.
Selective C-C bond cleavage under mild conditions can serve as a valuable tool for organic syntheses and macromolecular degradation. However, the conventional chemical methods have largely involved the use of noble transition-metal catalysts as well as the stoichiometric and perhaps environmentally unfriendly oxidants, compromising the overall sustainable nature of C-C transformation chemistry. In this regard, electrochemical C-C bond cleavage has been identified as a sustainable and scalable strategy that employs electricity to replace byproduct-generating chemical reagents. To date, the progress made in this area has mainly relied on Kolbe electrolysis and related processes. Encouragingly, more and more examples of the cleavage of C-C bonds via other maneuvers have recently been developed. This review provides an overview on the most recent and significant developments in electrochemically oxidative selective C-C bond cleavage, with an emphasis on both synthetic outcomes and reaction mechanisms, and it showcases the innate advantages and exciting potentials of electrochemical synthesis.
在温和条件下选择性地切断 C-C 键可以作为有机合成和高分子降解的有价值的工具。然而,传统的化学方法在很大程度上涉及使用贵金属过渡金属催化剂以及化学计量的、可能对环境不友好的氧化剂,从而影响 C-C 转化化学的整体可持续性。在这方面,电化学 C-C 键的断裂已被确定为一种可持续和可扩展的策略,它利用电力替代产生副产物的化学试剂。迄今为止,该领域的进展主要依赖于科尔贝电解和相关过程。令人鼓舞的是,最近越来越多的通过其他操作来切断 C-C 键的例子被开发出来。这篇综述概述了电化学氧化选择性 C-C 键断裂的最新和最重要的进展,重点介绍了合成结果和反应机制,并展示了电化学合成的固有优势和令人兴奋的潜力。