Due to many applications of C-N, C-O bonds formation in the areas including bioactive compounds, natural products and high performance materials, over the past few years, the coupling reactions such as C-N and C-O coupling have become a versatile tool in organic synthesis. In this work, the application of a green, efficient and inexpensive ionic liquid Copper(?) Chloride/Choline Chloride is studied. The ionic liquid; catalytic system has been developed to catalyze Palladium-free coupling reactions of arylamines or phenols with a variety of arylhalides to afford the corresponding coupling product in 50-97% yield. It has been found that electron-withdrawing substituents on arylhalides enhanced the coupling reactions, Excellent yield of the C-N and C-O coupling reactions catalyzed by 20% mol ionic liquid could be achieved at 140 ° C and DMSO as the solvent within 15-60 minutes. Previously, photoredox synthesis of indazoles for tetrahydroquinolines compounds was done with an expensive Ruthenium complex. In this project, It has been found that copper(?) Chloride/Choline Chloride has enough efficiency to react radical mechanisms reactions and can synthesis indazole compounds with photoredox mechanisms. The best result was found when acetonitrile as a solvent was selected and 20%mol catalyst was sufficient to afford 50-90% yield.
