The heterogeneous aminohydroxylation reaction using hydrotalcite-like catalysts containing osmium

Abstract

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.