Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido- tris(triphenylphosphine)ruthenium(II) Complex

The catalytic properties of several ruthenium, osmium and rhodium hydride complexes for hydrogen/deuterium (H/D) exchange between olefins and deuterium oxide (D 2 O) were investigated. The most effective catalytic precursor was found to be the carbonylchlorohydridotris(triphenylphosphine)-ruthenium(II) complex. Through H/D exchange between metal hydride and D 2 O, and reversible olefin insertion into an Ru―H(D) bond, protons attached to olefinic carbons and alkyl chains of olefins can all undergo H/D exchange with D 2 O. The catalytic reactions can be used to deuterate both terminal and internal olefins, for example, styrene, stilbene and cyclooctene.