C–N Cross Dehydrogenative Coupling Reaction Between Aryl Halides And Anilines Under Metal-free Conditions

Nitrogen-containing compounds are widely found in natural products,drugs andorganic synthesis intermediates.Among the nitrogen-containing compounds,amide is a key structural motif prevalence in biologically active molecules.C–N cross dehydrogenation coupling reaction is an effective way to synthesize amide due to the advantages of steps and atomic economy.The main contents of this paper are C–N cross dehydrogenation coupling reaction between aryl halides and anilides under metal-free conditions which might possess significant synthetic application value,the main contents are as follows.1.C–N bond was formed by oxidation cross dehydrogenation coupling of aryl halides and anilides under metal-free condition.In the presence of hypervalent iodine reagent,chlorobenzene or bromobenzene can be activated and undergo C-N cross dehydrogenation coupling with anilides.The reaction was carried out under easy operation,mild reaction conditions,have high product yield at room temperature.The retention of halogen atoms enables further transformations.2.C–N bond was formed by oxidation cross dehydrogenation coupling of iodoarenes and anilides under metal-free condition.The reaction was mediated by m CPBA without any metal catalysts or additives.The reaction exhibited high para-selectivity with retention of iodine atom which enables further transformations.This method also possessed the merits of substrates availability,easy operation and atom economy.It provided a simple and efficient route for the preparation of functionalized anilines.