Singha Hazari Arijit, Frisch Marvin L, Wen Yunzhou, Stankovic Mia D, Berlinguette Curtis P
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
Department of Chemical and Biological Engineering, The University of British Columbia, 2360 East Mall, Vancouver, British Columbia V6T 1Z3, Canada.
J Am Chem Soc. 2024 Oct 1. doi: 10.1021/jacs.4c07847.
Aromatic and aliphatic amines are key intermediates in the synthesis of pharmaceuticals, dyes, and agrochemicals. These amines are often sourced from nitro compounds. The hydrogenation of nitro compounds into amines requires harsh reaction conditions (e.g., high pressures and high temperatures) or additives that are usually toxic. Here we demonstrate the electrochemically-driven hydrogenation of nitro compounds into amines in the hydrogenation compartment of a membrane reactor. The hydrogen is sourced from water in an adjacent electrolysis compartment separated by a hydrogen-permeable palladium membrane. Modifications of the palladium membrane with catalyst coatings enabled a wide range of commercially relevant nitro compounds to be hydrogenated into amines, without any additives, at ambient pressure and room temperature. This membrane reactor also enables nitro hydrogenation at high reagent concentrations with high functional group tolerance.
芳香胺和脂肪胺是药物、染料及农用化学品合成中的关键中间体。这些胺类通常来源于硝基化合物。将硝基化合物氢化为胺需要苛刻的反应条件（如高压和高温）或通常有毒的添加剂。在此，我们展示了在膜反应器的氢化隔室中，通过电化学驱动将硝基化合物氢化为胺。氢气来源于由氢渗透钯膜隔开的相邻电解隔室中的水。用催化剂涂层对钯膜进行改性，能够在常压和室温下，无需任何添加剂，将多种具有商业相关性的硝基化合物氢化为胺。这种膜反应器还能够在高试剂浓度下进行硝基氢化反应，且对官能团具有高耐受性。
