Synthesis Of 1-(2-aminophenyl) Ethanone By Palladium/Norbornene Catalyzed

Catellani reaction is a domino reaction that catalyzed by palladium/norbornene,which can synthesize a range of aromatic compounds in one step and is of great interest in the synthesis of natural products and drugs.Since the first report of the Catellani reaction in 1997,various electrophilic reagents and quenching reagents have been developed.As a kind of important organic functional group,the synthesis of ketones has caught particular attention from synthetic organic chemists.At present,there are many literatures on the synthesis of aryl ketones.In this thesis,a new method of the synthesis of aryl ketones has been developed by using vinyl ethers as a quenching reagent in Catellani reaction.The first chapter introduces the development of the Catellani reaction.It can be terminated by Heck coupling,Suzuki coupling,Buchwald-Hartwig coupling,Sonogashira coupling,direct arylation,reduction and so on.We also revivewed the most recent developments concerning the Pd(II)-catalysed norbornene-mediated selective meta-C-H functionalization of arenes bearing commonly used ortho-directing groups,including applications in total synthesis of natural products.The second part,we describe a pallad ium/norbo rne ne-catalyzed ortho aminationand ipso vinyl ether termination reaction of iodoarenes is reported.We successfully used the N-benzoyloxyamine as electrophiles and the benzyl vinyl ether as an efficient alternative carbonyl source in palladium/norbornene catalysis for the final ipso termination reaction to give[1-(benzyloxy)vinyl]arenes,which readily undergo hydrolysis to deliver methyl ketones under aqueous acidic conditions.The final Heck termination reaction with vinyl ethers has high branched/linear selectivity.This reaction tolerates a range of iodoarene and O-benzoylhydroxylamine substrates,and it provides a convenient way to prepare o-acetylanilines.The synthetic utility of[1-(benzyloxy)vinyl]arenes and the corresponding ketones is briefly investigated,which are potentially useful in medicine,material science and other fields.