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The Heterogeneous Aminohydroxylation Reaction Using Hydrotalcite-Like Catalysts Containing Osmium

机译：含Hydro的水滑石类催化剂的非均相氨基羟基化反应

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The aminohydroxylation reaction of olefins is a key organic transformation reaction, typically carried out homogeneously with toxic and expensive osmium (Os) catalysts. Therefore, heterogenisation of this reaction can unlock its industrial potential by allowing reusability of the catalyst. Os–Zn–Al hydrotalcite-like compounds (HTlcs), as potential heterogeneous aminohydroxylation catalysts, were synthesised by the co-precipitation method and characterised by several techniques. Reaction parameters (i.e., solvent system, reaction temperature, and catalyst structure) were optimized with cyclohexene, styrene, and hexene as substrates. The different classes of olefins (aliphatic, aromatic, and functionalised) that were tested gave 99% conversion and high selectivity (97%) to the corresponding β-amino alcohol. The catalyst HTlc structure had a significant effect on the reaction time and yield of the β-amino alcohols. Under the same testing conditions, a heat treated catalyst (non-HTlc) showed a shorter reaction time, but drop in the yield of β-amino alcohols and rise in diol formation was observed. Leaching tests showed that 2.9% and 3.4% of Os (inactive) leached from the catalyst to the reaction solution when MeCN/water (1:1 v / v ) and t -BuOH/water (1:1 v / v ), respectively, were used as the solvent system. Recycling studies showed that the catalyst can be reused at least thrice, with no significant difference in the yield of the β-amino-alcohol.
机译：烯烃的氨基羟基化反应是关键的有机转化反应，通常使用有毒且昂贵的（Os）催化剂均相进行。因此，通过允许催化剂的可重复使用性，该反应的异质化可以释放其工业潜力。通过共沉淀法合成了Os-Zn-Al类水滑石化合物（HTlcs），作为潜在的非均相氨基羟基化催化剂，并通过多种技术对其进行了表征。以环己烯，苯乙烯和己烯为底物优化反应参数（即溶剂体系，反应温度和催化剂结构）。测试的不同种类的烯烃（脂肪族，芳族和官能化）对相应的β-氨基醇的转化率> 99％，选择性高（> 97％）。催化剂的HTlc结构对β-氨基醇的反应时间和产率有显着影响。在相同的测试条件下，热处理的催化剂（非HTlc）显示出较短的反应时间，但观察到β-氨基醇的产率下降和二醇形成的增加。浸出试验表明，当MeCN /水（1：1 v / v）和t -BuOH /水（1：1 v / v）时，分别有2.9％和3.4％的Os（惰性）从催化剂浸出到反应溶液中。用作溶剂系统。再循环研究表明，该催化剂至少可以重复使用三次，而β-氨基醇的收率没有显着差异。

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