Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

A practical and precise method for visible-light-promoted deoxygenative deuteration of common aliphatic alcohols using D2O as the deuterium source is reported. Upon intermediacy of xanthate anions, a variety of primary, secondary, and tertiary alcohols can be facilely transformed into deuterioalkanes with excellent D-incorporation at predicted sites. The deoxygenation and deuteration sequence is catalyzed by in situ formed deuterated 2-mercaptopyridine, which plays dual roles as a deuterium atom transfer catalyst and an electron shuttle as well.

Automated summary

A practical method for deoxygenative deuteration of aliphatic alcohols using D2O as the deuterium source is reported. The transformation is promoted by visible light and intermediacy of xanthate anions, leading to the formation of deuterioalkanes with high D-incorporation. The catalysis is carried out by in situ formed deuterated 2-mercaptopyridine, serving as a deuterium atom transfer catalyst and an electron shuttle.