The Deoxygenative Cross-coupling Reaction Of Carbonyl Compounds Under Electrochemical Conditions

Carbonyl（C=O）bonds,presenting as a prevalent structural and functional group in organic compounds,exist in many biologically active molecules,drugs and functional materials.Exploring the transformation of carbon-oxygen unsaturated double bonds has been bearing important academic and practical application value.Organic electrosynthesis is a scalable and green synthetic method,and the development of electrochemical synthetic approach for the conversion of carbonyl compounds can directly provide a new idea for reductive cross-coupling of C=O derivatives.In this thesis,the cross-coupling reactions of carbonyl compounds and（hetero）arenes were investigated using direct electrochemical catalysis.The detailed information is listed as follows:1.The deoxygenative cross-coupling of aromatic ketones and heteroarenes was realized using the synergistic catalysis of acid/silane under electrolytic conditions.The reaction with electron-rich heteroarenes proceeded smoothly and achieved the regioselective alkylation of aromatic rings.Through the optimization of electrochemical conditions,100% conversion of reactants and 82% isolated yield of standard product were obtained.The substrate scope as well as the reaction mechanism was explored under the optimal conditions.2.Under electrochemical conditions,carbonyl compounds are used as electrophilic alkylating reagents,which proceed cross-coupling reaction with electron deficient arenes（aromatic nitriles,N-heteroaromatics）smoothly.In the process of the electrochemical condition optimization,we were able to detect and successfully isolate three different coupling products.Subsequently,we carried out the investigation on the substrate scope.Preliminary insight on the reaction mechanism was disclosed by means of cyclic voltammetry（CV）,deuterated reagents and gas chromatography controlling experiments.In this thesis,we succeed the transformation of carbonyl compounds using two completely different reaction processes to construct new C-C bonds through electrochemical deoxygenative cross-coupling reactions.The new processes provides alternative strategy for carbonyl compounds transformation and new ideas for C-C bond construction.