Electrochemical Deoxidizing C2 Activation Of Quinoline-N-Oxide

Quinoline and its derivatives are valuable heterocyclic compounds and are largely present in biologically active natural products,synthetic pharmaceuticals and advanced functional materials.Owing to the significance of such a motif in a variety of fields,the development of practical protocols for the construction of various substituted quinolines has attracted considerable attention.Over the past few decades,numerous methodologies have been established for the C2 functionalization of quinoline N-oxides,which include the C–H bond alkylation,alkenylation,arylation,alkoxylation,acylation and acetoxylation,sulfonylation,phosphonation,amination,amidation,azidation,hydroxylation,halogenation,sulfhydrylation,and trifluoromethylation of quinoline N-oxides.However,the above reaction has problems such as excessive by-products or the use of a more toxic catalyst.,so it is of great significance to develop an efficient,green and environmentally friendly quinoline C2 functionalization method.Based on previous literature research,this paper uses electrochemical catalysis as a new,efficient,and non-polluting method to functionalize the C2 position of quinoline,avoiding the use of metal catalysts and stoichiometric oxidants.Based on the above research background,my work is mainly divided into the following two parts:1: This paper develops a simple and efficient method to realize the C2 arylation of quinoline without transition metals.The reaction is carried out in a three-neck integrated pool,using readily available sulfonyl hydrazide as an aryl source and using electrochemical catalysis to synthesize a wide range of natural products,pharmaceuticals,organic functional materials and synthetic intermediate The quinoline compounds,and the successful realization of the amplification reaction experiment,are extremely important for the future mass production in industrial production.2: This paper develops a simple and efficient method for the sulfonylation of quinoline without transition metals.The reaction was carried out in a three-neck integrated pool.A series of sulfonyl-substituted quinoline compounds were synthesized using non-toxic and readily available sodium sulfinate as the source of sulfonyl and electrochemical catalysis.The success of subsequent gram-level experiments proved that the method has the value of industrial production.This method is green,efficient,and safe,and avoids the shortcomings of traditional reactions(complex reaction processing,harsh conditions,environmental pollution,etc.).