Electrochemically Induced C-N Bond Coupling Reaction

The present work is divided into two parts:the first part introduces the researches on C-N coupling reaction via organic electrochemical strategies.Based on our laboratory's works,the secondary part realized C-N coupling reaction via electrochemically induced iodide salt catalyzed indirect oxidation or electrochemically induced direct oxidation strategies.1.Electrochemically induced KI catalyzed construction of ?-enaminone derivatesWe realized the intermolecular C(sp3)-H/N-H coupling reaction between cyclopentanone and anilines via electrochemical induction and KI catalysis,provided a green and efficient strategy for the construction of ?-enaminone derivates.The reaction avoids the addition of metal catalysis or chemical oxidant,features mild reaction conditions,easily available starting materials and high atom economy.DMPO was added to the EPR experiments to indirectly capture the free radical intermediate,indicating the mechanism of radical process.2.Electrochemically induced iodine catalyzed construction of indoline derivatesWe realized the intramolecular C(sp2)-H/N-H coupling reaction from 2-vinyl anilines via electrochemical induction and iodine catalysis,provided a a green and efficient method for the synthesis of indoline derivates.The reaction avoids the addition of metal catalysis and oxidant,features mild reaction conditions,high yields,broad substrate scopes,high compatibility of functional groups,gram-scale experiment with yield maintained,has a certain value in industrial application.3.Electrochemically induced iodine catalyzed constrution of indole derivatesWe achieved the intramolecular C(sp2)-H/N-H coupling reaction from 2-vinyl anilines via electrochemical induction and iodine catalysis,provided a pratical and convinient mean for the synthesis of functionalized indoles.The reaction features no addition of metal catalysis and stoichimetric oxidant,mild reaction conditions,high yields,broad substrate scopes,high compatibility of functional groups,gram-scale experiment with yield maintained and good practicality,potential application in large-scale indudtrial production.4.Electrochemically induced direct oxidation formation of pyrazol derivatesWe performed the intramolecular C(sp2)-H/N-H coupling reaction from?,?-unsaturated hydrazone via electrochemically direct oxidation,provided a rapid and highly efficient method for the synthesis of pyrazol derivates.The reaction features no addition of metal catalysis and additional oxidant,only substrate and electrolyte,mild reaction conditions,high reaction yields,wide substrate scopes and high atom economy.Compared with the traditional methods,the electrochemically induced C-N coupling methods avoid or decrease the use of metal catalysis and oxidant.The method features high atom economy,green and efficient.The iodide salt,employed as both electrolyte and mediator,shows important research significance and application value in electrochemically induced C-N coupling reactions.