Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

Beilstein J Org Chem. 2024 Jul 11:20:1560-1571. doi: 10.3762/bjoc.20.139. eCollection 2024.

Abstract

An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA.

Keywords: PEM reactor; cyanoarene; nitroarene; pyridine; quinoline.

Grants and funding

This work was supported in part by JST CREST Grant No. JP65R1204400, Japan, JSPS KAKENHI Grant Numbers JP22H02122 (to K.M.), JP23K17917 (to K.M.), JP22K05115 (to S.S.), and JP21H05214 (Digitalization-driven Transformative Organic Synthesis) (to S.S.),