摘要：Rok Narobe, Marcel Nicolas Perner, María de JesúsGálvez-Vázquez, Conrad Kuhwald,Martin Klein, Peter Broekmann, Sina Rösler, Bertra

转自：康龙化成

Practical Electrochemicalhydrogenation of nitriles at the Nickel foam Cathode

Rok Narobe, Marcel Nicolas Perner, María de JesúsGálvez-Vázquez, Conrad Kuhwald,Martin Klein, Peter Broekmann, Sina Rösler, Bertram Cezanne andSiegfried R. Waldvogel*

Department of Chemistry, JohannesGutenberg University Mainz, 55128 Mainz, Germany

Max-Planck-Institute for Chemical EnergyConversion, Stiftstraße34–36, 45470 Mülheim ander Ruhr, Germany

—Green Chem., 2024, 26,10567-10574.

Recommended by Shi Li_MOC

KEYWORDS:Electrochemistry, hydrogenation,flow chemistry (反应类型), C(sp3)–N (成键类型),nitrile(原料),primary amines (产物),nickelfoam, cathode reduction,galvanostatic condition(其他)

ABSTRACT: Siegfried R. Waldvogel et al reported a scalable hydrogenation method for nitriles based on cost-effective materials in a very simple two-electrode setup under galvanostatic conditions. All components are commercially and readily available. The method is very easy to conduct and applicable to a variety of nitrile substrates, leading exclusively to primary amine products in yields of up to 89% using an easy work-up protocol. Importantly, this method is readily transferable from the milligram scale in batch-type screening cells to the multi-gram scale in a flow-type electrolyser. It is noteworthy that this method is sustainable in terms of process safety and reusability of components

Background and this work

Optimizationof the reaction conditions

Synthetic scope

SiegfriedR. Waldvogel et al report an operationally very simpleelectrochemical method for the hydrogenation of nitriles, which is readilyscalable and advantageous in terms of sustainability. Thismethod is applicableto non-conjugated aliphatic nitriles and aromatic benzylcyanide derivatives. Incontrast to other electrochemical hydrogenation methods, it relies on the useof a practical 2-electrode setup and readily available commercial materials andcomponents. The use of inexpensive nickel foam asthe cathode material offers an important advantage in terms of scalability dueto its availability and excellent mechanical properties. To capitalize on this,they show the ease of scalability from batch-type screening cells to twodifferently sized flow cells, eventually reaching a notable productivity of 20g day−1 of phenylethylamine. Reusability studies showed that nickel electrodescan be reused many times without a significant drop in performance.

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