Reaction Study Of Constructing Nitrogen-Containing Small Molecules Based On Amine Compounds

1.Aryl amination with iron and boronAromatic amine compounds serve as common key building blocks in organic synthesis due to the diversity of their reactivity.It is also ubiquitous in important organic molecules.Currently,C-N bonds are constructed by using transition metal-catalyzed C-H bond-activated amination under the action of guiding groups.Here,we developed a method for directing CH bond amination by iron-catalyzed reaction of N-hydroxyphthalimide to construct arylamines in the presence of bisboronic esters.A total of 17 examples were developed in this project,including aromatic compounds with different electrical substituents,with moderate to good yields.2.Aryl amination with copper and phosphiteArylamines are ubiquitous in pharmaceutically active molecules and multifunctional materials.Deoxygenation reactions are a fundamental transformation in organic synthesis and biochemistry,and the established methods for direct deoxygenation conversion reactions involve the use of low-valent metals and halide ions.Therefore,we developed an efficient method for the synthesis of aromatic amines by the deoxygenation of phosphites,coppercatalyzed N-hydroxyphthalimide.The reaction conditions are mild and the substrate range is wide.A total of 21 examples have been developed in this project,including aromatic compounds with different electrical substituents,with moderate to good yields,and a few heterocyclic compounds can also be successfully reacted in general yields.3.Copper-catalyzed reaction of constructing oxazole ringsOxazole derivatives are the main backbones in many natural products as well as biologically active compounds.Although many strategies have been developed for the synthesis of oxazoles,such as oxidative cyclization,transition metal-catalyzed addition of diazonium compounds to nitriles and rearrangement reactions.A new method for the construction of oxazole derivatives from starting materials without prefunctional activation is still valuable.Therefore,we realized the synthesis of a series of 5-oxazolone derivatives using benzylamine as nitrogen source and copper-catalyzed simple arylacetonides.A total of 23 substrates were expanded in this reaction,and the substrates substituted by electron-donating groups and electron-deficient groups were tolerated.The yields were moderate to good.A few substrates substituted by heterocycles were also obtained in moderate yields.