Nickel-catalyzed Selective Bifunctionalization Of Non-activated Alkenes

The use of readily available alkene as inexpensive building blocks for constructing new chemical bond is a powerful and well-established method in organic synthesis.Transition meta-catalyzed functionalization of alkenes is among the most eficient synthesis combining atom economy and ability to generate molecular complexity.Similarly,it can form some new carbon-nitrogen bonds and carbon-carbon bonds,which has great significance in organic synthesis.Therefore,the main research work of my dissertation is based on the Ni-catalyzed the selective difunctionalization of non-activated olefins.In the first part of my work,I have used 3-butenamine with a removable bidentate group as the substrate and reacted with aryl boronic and aryl iodide to get 2,1-regioselective product through diarylation.After that,I have extended the scope of iodide to alkyl iodide and the resulting products still have 2,1-regioselectivity through arylalkylation.In the second part of my work,I have used enamine with a removable bidentate group as the substrate and reacted with aryl boronic and amine benzoate to get1,2-regioselective product through arylamination.The resulting products with high levels of diastereoselectivity and a series of primary and secondary amines can be used as coupling substrates to participate in the reaction.In addition,the method can also be applied to the late-stage regio-and diastereoselective functionalization of some pharmacologically related complex molecules,which provides a new way for the facile synthetic of biorelevent macromolecules.From a comprehensive point of view,the establishment of these synthetic methods has provided a novel synthetic approach to form the new carbon-carbon and new carbon-nitrogen.For another,this research explores the possibility of difunctionalization reaction with picolinic acid as the directing group under cheap transition metal conditions,laying the foundation for the further research on the use of different directing groups for difunctionalization under transition metal conditions.