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Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds

Title	Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds
Authors	Naoki Shida, Yugo Shimizu, Akizumi Yonezawa et al.
Magazine	Journal of the American Chemical Society
Date	10/07/2024
DOI	10.1021/jacs.4c09107
Introduction	The creation of cyclic amines, crucial for pharmaceuticals, traditionally depends on energy-intensive thermochemical hydrogenation. This study showcases the ambient temperature and pressure electrocatalytic hydrogenation of nitrogen-containing aromatic compounds such as pyridine using a membrane electrode assembly with an anion-exchange membrane. Using a carbon-supported rhodium catalyst, we achieved a current density of 25 mA cm–2 and a high current efficiency of 99% in a circular flow until 5 F mol–1. A quantitative conversion of pyridine to piperidine with a 98% yield was recorded after 9 F mol–1, equivalent to a 65% current efficiency. The reduction of Rh oxides on the catalyst surface was pivotal, as the Rh(0) surface interacts with piperidine, reducing energy for the rate-determining desorption step. This process is applicable to other nitrogen-containing aromatic compounds and could be effectively scaled, offering advantages over conventional high-temperature and high-pressure catalytic methods.
Quote	Naoki Shida, Yugo Shimizu and Akizumi Yonezawa et al. Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds. J. Am. Chem. Soc. 2024. Vol. 146(44):30212-30221. DOI: 10.1021/jacs.4c09107

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