Advances in Electrochemical Cathodic Reductive Reactions Involving Carbon-Nitrogen Bonds
Compounds containing carbon-nitrogen bonds,such as amines,imines,nitriles,and N-heterocycles,are widespread in nature and play essential roles in pharmaceuticals,pesticides,materials,and other fields.The investigation of reactions in-volving carbon-nitrogen bonds is of paramount significance.In organic synthesis,the reduction of carbon-nitrogen bonds can be used for the removal of protecting groups,conversion of functional groups,and construction of biologically active molecules.However,carbon-nitrogen bonds,especially carbon-nitrogen single bonds,are renowned for their notable stability,thus requiring the harsh conditions for their reductions.As the renaissance of organic electrosynthesis in recent years,the elec-trochemical cathodic reductive reactions of carbon-nitrogen bonds under mild conditions have garnered considerable attention.According to the molecular structure of the substrates,electrochemical cathodic reductive reaction involving carbon-nitrogen bonds can be classified into two major categories:reductions of saturated carbon-nitrogen bonds,and unsaturated carbon-nitro-gen bonds.For compounds with saturated carbon-nitrogen bonds,such as ammonium salts,amides,aziridines,and nitro com-pounds,their cathodic reductions usually involve the cleavage of carbon-nitrogen bonds and substitution of the N-contained functional group.Compounds with unsaturated carbon-nitrogen bonds,such as imines,oximes,and N-heterocycles,are typi-cally reduced into intermediates containing carbon-nitrogen single bonds,followed by addition reactions.A concise overview of the cathodic reductive reactions of above two kinds of substrates is provided and the possible reaction mechanisms is sum-marized.
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