"On Water" Mediated Nucleophilic Addition Reaction Of Acyl Compounds

Water is the cheapest,safest,and most environmentally benign solvent in nature.Use of water as reaction medium will reduce the use of harmful organic solvents and represents an important subject in green chemistry.In addition,water also has unique physical and chemical properties,which shows completely new reactivity as compared to traditionally organic solvents.Therefore,the use of water as reaction medium has attracted wide attention of organic chemists.In our research,we devoted to the development of new,efficient and green “on water” reaction.Aiming at nucleophilic addition reactions of acyl compounds,we completed the following progress:1.An “on water” organocatalytic cyanoarylmethylation of aryl acetonitrile to isatins is developed,giving the corresponding products in high yields with up to excellent diastereoselectivities.Moreover,this approach has good substrate applicability,and provides a highly efficient and environmentally benign access to 3-hydroxy-3-cyanomethyl oxindoles.At the same time,time-dependent dr changes of some products were observed in this on water catalytic process,which have been well explained via DFT calculations.2.We have developed an “on water” mediated nucleophilic addition of pyrazolones to trifluoromethyl ketone.This catalyst-free and column chromatography-free approach provides a highly efficient and environmentally benign access to provide various pyrazolone substituted tertiary trifluoromethyl alcohols,which show good application prospects.