The Reactivities Study Of IBX Derivatives IBS And AIBX

Catalytic oxidation of benzylic C-H bond could be efficiently realized using IBSas a catalyst which was generated in situ from the oxidation of sodium2-iodobenzenesulfonate by Oxone in the presence of a phase-transfer catalysttetra-n-butylammonium hydrogen sulphate in anhydrous acetonitrile at60oC.Various alkylbenzenes, including toluenes and ethylbenzenes, several alkylbenzeneswith oxygen-containing functionalities, and a cyclic benzyl ether could be efficientlyoxidized. And, the same reagent system could be applied to effective oxidation ofalkanes as well.Water soluble IBX derivatives AIBX bearing trimethylammonium groupthrough a covalent bond were designed and synthesized for the first time. All of themwere characterized by NMR, IR and HRMS, and single crystal diffraction for one ofthem. AIBX possess very good solubility in water and distinct oxidative propertyfrom IBX, which is demonstrated in the oxidation of various β-keto esters to thecorresponding dehydrogenaated products using water as co-solvent. The regenerationof AIBX can be easily realized from the reaction mixture due to its good watersolubility.The construction of2,3-dihydrofuran skeleton can be realized by AIBXmediated C-C and C-O bonds coupling of β-keto ester of indanone and dimedone in ahomogenous solution of CH3CN and water at40oC. Under this condition, manyβ-keto esters of indanones with vried substitution pattern could be react smoothlywith various active methylene nucleophiles, delivering the corresponding products ingood to excellent yields.