Merging Electrocatalytic Alcohol Oxidation with C-N Bond Formation by Electrifying Metal-Ligand Cooperative Catalysts

Abstract

The development of energy and atom efficiency processes is thought to play an important role for a sustainable chemical industry of the future. One opportunity could be the electrification of thermal processes to benefit from the inherent advantages of electrochemistry, such as safety, scalability, a cheap and traceless redox agent (electrons), and the possibility to directly control the energy input of a given reaction via the applied potential. Molecular electrocatalytic alcohol oxidation emerged as a powerful tool for energy efficient redox transformations with possible applications in both green synthesis and energy-relevant domains. Using transfer hydrogenation catalysts under electrochemical conditions was shown to be promising avenue in this respect, but is today limited in terms of substrate scope. Here, we reported the electrification of acceptor-less dehydrogenation catalysts for the coupling of alcohol oxidation with C-N bond formation. Imines are thus obtained with excellent selectivity and faradaic efficiency, showing a possibility route towards added-value products from simple building blocks. We hope that the successful electrification of such atom-efficient systems can contribute to a more energy efficient organic redox chemistry.

Electrochemical nitration for organic C–N bond formation: a current view on possible N-sources, mechanisms, and technological feasibility

“…Since multiple classes of target molecules such as monomers, pesticides, and pharmaceuticals possess C–N bonds, 26 the formation of these bonds by electrochemical methods is receiving increasing attention. 27–33 In 2018, Kärkäs presented a comprehensive review article describing electrochemical C–H activation for, among other things, C–N functionalization. 34 Most of the included studies consider organic nitrogen sources (N-sources), i.e.…”