Hydrogen Isotope Exchange of Multisubstituted Alkenes Catalyzed by Zeolite

Abstract

Olefins are widely present in natural products and synthetic drugs, and also serve as building blocks in organic synthesis. However, deuterated multisubstituted alkenes are rarely reported, owing to structural limitations for the reduction of corresponding alkynes and lack of efficient hydrogen isotope exchange methods for such alkenes caused by steric hindrance. Herein, we have developed an efficient, convenient zeolite-catalyzed hydrogen isotope exchange reaction for multisubstituted olefins via reversible addition of proton to alkenes in D2O solvent. This novel approach affords a wide range of deuterated multisubstituted alkenes through a simple separation operation with the use of commercially available catalyst and D2O.