Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h(-1). Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

Automated summary

This study focuses on developing a green system for the asymmetric transfer hydrogenation of ketones using chiral Ru catalyst in aqueous media and mechanochemical energy transmission. The scale-up of the system was successful with high yields of optically enriched alcohols. The developed mechanochemical system provides high TOFs up to 168 h(-1), making it a useful guide for the practical synthesis of optically pure chiral secondary alcohols.