Cathode–Anode Synergy Electrosynthesis of Propanamide via a Bipolar C–N Coupling Reaction

IF 14.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Ming-Hao Guan, Hao-Nan Xu, Jin Liu, Xiao-Ya Zhou, Tao Wu, An-Hui Lu
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Abstract

Propanamide is a crucial synthetic intermediate in pharmaceuticals for the preparation of antibacterial and anticancer drugs. Conventional synthesis of propanamide involves the reaction of carboxylic acid derivatives with amines, which requires harsh reaction conditions, leading to an unfavorable environmental footprint. Here, we present a cathode–anode synergistic electrochemical strategy to transform nitrate and n-propanol into propanamide under ambient conditions, where both the cathode catalyst Co3O4/SiC and the anode catalyst Ti contribute distinctively to the electrochemical process. The CH3CH2CHO produced at the Ti anode can diffuse and react with the adsorbed intermediate *NH2OH on the surface of the cathode catalyst to form propanamide. The synergistic reactions at both electrodes collectively enhance the efficiency of the propanamide synthesis. This design enables efficient propanamide production in a flow cell at the gram scale with a remarkable yield of 986.13 μmol/(cm2·h) at current densities of up to 650 mA/cm2. Our reports present a new option for environmentally friendly C–N bond synthesis, and the insights can be useful for the electrosynthesis of a wider scope of amides.

Abstract Image

阴极-阳极协同电合成丙酰胺的双极性C-N偶联反应
丙酰胺是制备抗菌和抗癌药物的重要合成中间体。传统的丙酰胺合成涉及羧酸衍生物与胺的反应,反应条件苛刻,导致不利的环境足迹。在此,我们提出了一种在环境条件下将硝酸盐和正丙醇转化为丙酰胺的阴极-阳极协同电化学策略,其中阴极催化剂Co3O4/SiC和阳极催化剂Ti都对电化学过程有独特的贡献。在Ti阳极产生的CH3CH2CHO可以扩散并与阴极催化剂表面吸附的中间体*NH2OH反应生成丙酰胺。两个电极上的协同反应共同提高了丙酰胺合成的效率。该设计能够在流速池中以克为单位高效生产丙酰胺,在高达650 mA/cm2的电流密度下,产率可达986.13 μmol/(cm2·h)。我们的报告为环境友好的C-N键合成提供了一种新的选择,并且这些见解可以用于更广泛的酰胺的电合成。
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来源期刊
CiteScore
24.40
自引率
6.00%
发文量
2398
审稿时长
1.6 months
期刊介绍: The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
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