Research Of Synthesis Novel Phosphine-oxazole Compounds And Its Application As The Ligand

Ligand can effectively improve the catalytic activity and selectivity of metal catalysts.Bisdentate ligands of phosphonoxazole type are widely used in transition metal catalysis due to their hemilability.Active reagents and strong acids such as N-butyl lithium,zinc chloride and hydrochloric acid are often used in the traditional synthesis of phosphine-oxazole compounds.Phosphine-containing ligands are often unstable in the air,resulting in the development of their applications.In this paper,using copper acetate as catalyst and oxidant,naphthoquinone,phosphonoxycompound and imine were synthesized by one-pot method,and a series of new phosphine-oxazole ligands were synthesized by simple transformation.On this basis,N-monoalkylation of amine or nitrobenzene with alcohol catalyzed by palladium was achieved by using the new phosphine-oxazole ligand.The specific research contents are as follows:(1)In this paper,Cu-Catalyzed reaction of in situ generated C-Phosphoryl hydro naphthoquinone and imide was reported.Naphthalene oxazolphosphine was synthesized by one pot method of 1,4-naphthoquinone,phosphine oxide and imine.The method has good applicability for alkyl or arylphosphonoxides and arylimine,alkylimine,heterocyclic imines and other substrates.In addition,the system is also applicable to aryl or alkyl-terminal alkynes.Through simple and efficient methylation and reduction reaction,the phosphine-oxazole ligand can be converted into potential value.The good yield of the amplification reaction also proves the feasibility of the application of the reaction.(2)The application of a novel phosphonoxazole ligand in palladium-catalyzed N-mono alkylation was reported.The reaction use amine or nitrobenzene as N1 source and alcohols as C1 source.As a new PHNBOX ligand,phosphine-oxazole ligand can be used to synthesize N-mono alkyl amines with high selectivity and high yield.Through the comparison of a series of phosphine,nitrogen ligands and PHNBOX ligands with different structures,the excellent properties of PHNBOX ligands and the influence of ligand structure on the catalytic reaction were demonstrated.