A novel, efficient and reusable heterogeneous catalytic assembly of peroxophosphotungstate held in an ionic liquid brush was synthesized and an extraction and catalytic oxidative desulfurization (ECODS) procedure was developed for a model oil of benzothiophene (BT) and dibenzothiophene (DBT) using 30 wt% hydrogen peroxide as terminal oxidant and methanol as solvent under mild conditions. Several factors that affect sulfur removal were investigated in detail. The highest sulfur removal can reach 100% for BT in 7 h at 70 °C when the molar ratio of H₂O₂, S and catalyst is 10:1:0.025. The sulfur removal for DBT can also reach 100% in 4 h at 50 °C with the same molar ratio of H₂O₂, S and catalyst. The experimental results demonstrate that this ECODS process has no apparent scale-up effect. The catalyst can be easily recovered (via simple filtration) and recycled five times without a significant decrease in activity. Copyright © 2015 John Wiley & Sons, Ltd.

A reusable heterogeneous catalytic assembly of [PO₄{WO(O₂)₂}₄]³⁻ held in an ionic liquid brush was synthesized and an environmentally friendly procedure was developed for the dihydroxylation of several olefins with 30 wt% H₂O₂. These reactions were conducted in neat water under mild conditions without any organic co-solvent or other additive. Several factors that affect the dihydroxylation were investigated in detail. The catalyst is easily recovered after the reaction via simple filtration, and can be reused at least eight times without a noticeable loss of activity. The experimental results demonstrate that this dihydroxylation process has no apparent scale-up effect. Copyright © 2014 John Wiley & Sons, Ltd.

The urea-catalyzed aziridination of 1,2-vicinal haloamines derived from aminohalogenation of olefins has been developed. This rapid and simple method was carried out by simply grinding the solid mixture of the substrate, K₂CO₃ and catalytic amount of urea at room temperature in air. The reaction provides a protocol for quantitative preparation of aziridines in a large scope of aminohalogenated derivatives of olefins including α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins. The possible mechanism involving an H-bond promoting deprotonation has been suggested for this reaction.

A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry.

(+)-Tartaric acid-catalyzed aminobromination of α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins utilizing TsNH₂/NBS as the nitrogen/halogen sources at room temperature without protection of inert gases achieved good yields (up to 92% yield) of vicinal haloamino products with excellent regio- and stereoselectivity, even just 10% of (+)-tartaric acid was used as catalyst. The regio- and stereochemistry was unambiguously confirmed by X-ray structural analysis of products 2b and 12c. The electron-rich and deficient olefins show significant differences in activity to the aminobromination reaction and give the opposite regioselectivities. The 21 cases have been investigated which indicated that our protocol has the advantage of a large scope of olefins. Additionally, tartaric acid as catalyst has the advantage of avoiding any hazardous metals retained in products.

The regio- and stereoselective aminobromination of α,β-unsaturated carbonyl compounds and simple olefins catalyzed by elementary aluminium powder has been established by using p-toluenesulfonamide (TsNH₂) and N-bromosuccinimide (NBS) as the nitrogen/bromine sources. The reaction was convenient to carry out with a loading of 1 mol% catalyst at room temperature without inert gas protection. This method provides an easy approach to trans vicinal haloamino derivatives of α,β-unsaturated carbonyl compounds and simple olefins in high yields (up to 99.8%) and in excellent regio- and stereoselectivities. The electron-rich and electron-deficient olefins show significant differences in activity to the aminobromination reaction and give the opposite regioselectivities. Two possible pathways involving separately a bromonium or an aziridinium intermediate have been proposed.