Gold-catalyzed Nucleophilic Cyclization/Rearrangement Reactions For The Synthesis Of Inden-1-ones

Inden-1-ones,are valuable synthetic intermediates and important structural units found in natural products,pharmaceutical molecules and functional materials.So they have very important application values.Recently,many methods have been developed,including the Friedel-Crafts reaction,Nazarov cyclization and transition metal-catalyzed annulation.However,these methods generally require the use of at least an equivalent amount of Lewis acid.Besides,these methods usually with harsh reaction conditions.This paper amis to research alcohols induced Au-catalyzed dimerization of(2-ethynylaryl)methanols through rearrangement and Au-catalyzed rearrangement of 1-(2-(1H-isochromen-3-yl)aryl)ethanones with alcohols.These reactions with high atom economy and environmental friendliness,which have been developed for cheaply and effectively synthesis of heterocyclic compounds.The dissertation include the following results.1 This paper described that AuBr3 can catalyze the dimerization and carbocyclization of(2-ethynylaryl)methanols with alcohols,which lead to 2,3-dihydro-1H-inden-l-ones in moderate to good yields.The present cyclization method proceeds through nucleophilic addition,dimerization,benzylic C-H activation,oxygen-migration and skeletal rearrangement,which provides a new approach for the preparation of five-membered carbocycles.2 This paper established a novel and simple method for the construction of 2,3-dihydro-1H-inden-1-ones based on gold-catalyzed nucleophilic addition,oxygen-migration and skeletal rearrangement sequence.Importantly,this unexpected rearrangement method provides a new synthetic utility for gold catalyzed.Moreover,the mechanism was discussed according to the 18O-labeled experiments and the results presented.