A series of asymmetric monoimidazolium dihydroboronium-based ionic liquids (ILs) were synthesized from amine-boranes. All the resulting ILs were fully characterized by ¹H and ¹³C NMR, IR spectroscopy, elemental analysis or high resolution mass spectrum. Compared with the symmetric bisimidazolium dihydroboronium-based ILs, these new ILs exhibited improved properties with shorter ignition delay times (IDs), higher densities, and lower phase transition temperature showing the promising application potential as green propellants.

Chiral keto nitriles (β-cyano ketones) have been prepared by a facile and efficient asymmetric conjugate hydrocyanation of poorly active chalcone-type enones with benzophenone cyanohydrin. Using in situ generated 5–10 mol-% of sodium (S)-6,6′-di(1-adamantyl)-1,1′-binaphthyl-2,2′-diyl phosphate as catalyst and 5–10 mol-% of 2-tert-butylphenol as an additive, high yields and excellent enantioselectivities were obtained within 2 h in toluene at 80 °C. The development of catalysts, optimization of the reaction parameters, and substrate scope are reported. On the basis of the experimental results, HCN is shown to be the real cyanide source and a mechanism is proposed to explain the origin of the enantioselectivity with the chiral-anion-modified nucleophile HCN.

An efficient 1,4-addition of Me₃SiCN to aromatic enones has been achieved with excellent yields (91% –99%) using CsF (1 mol%) as the catalyst and H₂O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselectivity is proposed accounting from H₂O-facilitated reversion of the 1,2-adduct in the presence of CsF and subsequent irreversible 1,4-addition reaction.