Visible Light Induced Synthesis Of N-aryl Glycine Esters

N-aryl glycine esters are common amino acid esters in our life.It can be used for the synthesis of natural products and drug molecules,such as 1,2,3-triazole compounds,quinoline fused lactones,quinolone-2-carboxylate,and 1,3-oxazine derivative.The N-aryl glycine ester can be hydrolyzed to obtain N-aryl glycine,which can synthesize amino acid derivatives,such as N-phenyl glycine hydrazide.This dissertation focuses on the synthesis of N-aryl glycine ester by visible light induction.N-phenyl glycine ester compounds were obtained by visible light induction with ethyl diazoacetate and aniline as raw materials,iridium complex as photocatalyst and Iron(II)trifluomethanesulfonate as additive at room temperature.After optimizing the reaction conditions,the yield reached 66%.Under these conditions,the substrate of 48 aromatic amines was expanded,and 33 N-aryl glycine ester compounds containing benzene ring and nitrogen heterocyclic ring were obtained with the yield of 20%-78%.The experiment results are analyzed from electron effect and space effect,and the corresponding conclusions are drawn.The possible mechanism was obtained by fluorescence quenching and free radical capture experiment.The possible reaction mechanism is that after the metal iridium catalyst absorbs energy,it excites the complex formed by ethyl diazoacetate and Iron(II)trifluoromesylate,generates iron carbine,forms a bond with N atoms on aryl amine,and forms a intermediate compound containing Iron(II),which decomposes to obtain N-aryl glycine ester.