IBX衍生物IBS及AIBX反应性研究
摘要
我们成功地发展了一个以邻碘苯磺酸钠为催化剂，以Oxone为最终氧化剂，以四丁基硫酸氢铵为相转移催化剂的苄位碳氢键催化氧化体系。包括甲苯、乙苯在内的一系列烷基苯都可以顺利地被氧化到相应的羰基化合物。该体系还可用于饱和烷烃碳氢键的催化氧化。
我们首次设计并合成了三甲基铵盐基团通过共价键直接与IBX苯环相连的水溶性IBX衍生物AIBX，并通过核磁、红外、高分辨以及单晶衍射等手段对AIBX进行了表征。AIBX不仅具有良好的水溶性，而且可以在水相中将一系列环状β-酮酸酯氧化到相应的脱氢产品，这一点与IBX是截然不同的。AIBX良好的水溶性使其很容易实现再生回收。
我们发展了一个通过AIBX氧化茚酮β-酮酸酯与dimedone发生C-C键以及C-O键偶联来构建2,3-二氢呋喃骨架的方法。在此反应条件下，一系列带有不同取代基的茚酮β-酮酸酯与含有活化亚甲基的亲核试剂都可以顺利地发生反应。
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.
我们首次设计并合成了三甲基铵盐基团通过共价键直接与IBX苯环相连的水溶性IBX衍生物AIBX，并通过核磁、红外、高分辨以及单晶衍射等手段对AIBX进行了表征。AIBX不仅具有良好的水溶性，而且可以在水相中将一系列环状β-酮酸酯氧化到相应的脱氢产品，这一点与IBX是截然不同的。AIBX良好的水溶性使其很容易实现再生回收。
我们发展了一个通过AIBX氧化茚酮β-酮酸酯与dimedone发生C-C键以及C-O键偶联来构建2,3-二氢呋喃骨架的方法。在此反应条件下，一系列带有不同取代基的茚酮β-酮酸酯与含有活化亚甲基的亲核试剂都可以顺利地发生反应。
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.
引文
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