On water Catalytic Michael Addition Between α,β-Unsaturated Ketone and Nitromethane

The first systematic on water Michael addition between alpha,beta-unsaturated ketone and nitromethane has been developed, credited to the introduction of an extra hydrogen bond forming site, N-methyl imidazole group, which is adjacent to the carbonyl group of ketones with their electrophilic activity enhanced. Moreover, a reaction rate enhancement was observed on water than in other organic solvents. In addition, the solvent deuterium isotope effect test and contact angle measurement indicate that N-methyl imidazole bearing substrates are prone to form hydrogen bonds with water. Our results not only expand the reaction scope of on water catalysis, but also provide insight for selecting suitable substrates for on water reactions. [GRAPHICS] .

Automated summary

A novel systematic on water Michael addition reaction using alpha,beta-unsaturated ketone and nitromethane was developed by introducing an N-methyl imidazole group to enhance electrophilic activity, leading to a higher reaction rate in water. The results suggest that N-methyl imidazole bearing substrates are prone to form hydrogen bonds with water, providing insights for selecting suitable substrates for on water reactions.