Electrochemical Dicarboxylation of Vinyl Epoxide with CO2 for the Facile and Selective Synthesis of Diacids

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Deyong Yang, Ying Sun, Nan Feng, Yuqing Zhong, Prof. Dr. Jian Zhou, Prof. Dr. Feng Zhou
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Abstract

We present a novel electrochemical dicarboxylation of epoxides with CO2, characterized by the cleavage of two C−O single bonds. Not only are vinyl epoxides viable, but cyclic carbonates also serve as effective substrates, facilitating the synthesis of E-configured adipic and octanedioic acids with high chemo-, regio-, and stereoselectivity. The synthetic practicality is further highlighted by the diverse functionalizations of the resulting multifunctional diacids. Mechanistic studies support the single-electron transfer reduction of CO2 to its radical anion, which undergoes radical addition to the vinyl moiety of epoxides. The subsequent reductive cleavage of two C−O bonds, coupled with a nucleophilic attack on CO2, culminates in the formation of the desired diacid products.

Abstract Image

环氧乙烷与CO2的电化学二羧化反应,以方便和选择性地合成二酸
我们提出了一种新的环氧化合物与CO2的电化学二羧基化反应,其特征是两个C-O单键的断裂。不仅乙烯基环氧化物是可行的,而且环状碳酸盐也可以作为有效的底物,促进合成具有高化学选择性、区域选择性和立体选择性的E -构型己二酸和辛二酸。合成的实用性进一步突出了所得到的多功能双酸的多种功能化。机理研究支持二氧化碳的单电子转移还原到它的自由基阴离子,它经历自由基加成到环氧化物的乙烯基部分。随后两个C-O键的还原裂解,加上对CO2的亲核攻击,最终形成所需的二酸产物。
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来源期刊
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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