Study On Aryl Iodine Catalyzed Oxidative Cleavage Of Olefins

In this thesis,aryl iodine catalyzed oxidative cleavage of olefins to corresponding carbonyl compounds was studied,The results are as follow:The oxidative cleavage of olefins has been developed using aryl iodine as catalyst,fluoroboric acid as additive and m-chloroperoxybenzoic acid as oxidant under mild conditions to give the corresponding aldehydes / ketones in good to excellent yields.(Scheme 1).First,high-valent active aryl iodine species is formed via oxidation of aryl iodide using m-chloroperoxybenzoic acid and subsequent activation of olefin by coordinating.Further oxidative cleavage of active olefin to generate the corresponding aldehyde / ketone(Scheme 2).Olefins can be oxidized to the corresponding aldehydes / ketones selectively using aryl iodine as catalyst under mild conditions.Control experiments were performed to clarify the mechanism of oxidation process.(Scheme 3).Under the optimized oxidation reaction condition:styrene(0.2 mmol),iodobenzene(0.2 eq),m-CPBA(2.2 eq),HBF4(2.2 eq),toluene(1.2m L)and water(0.4 m L),30 ?,1-6 h,the scope of the substrate was examined.Under the optimized oxidation reaction condition: oledin(0.2 mmol),iodobenzene(0.2 eq),m-CPBA(2.2 eq),HBF4(2.2 eq),toluene(1.2 m L),water(0.4 m L)and hexafluoroisopropanol(HFIP)(0.4 m L),35 ?,4 h,substituted olefins can be oxidative cleavage to corresponding ketones the scope of the substrate was examined.Transformation of the generated dicarbonyl compounds was investigated.(Scheme 4).