%0 Generic %A Bai, Wei %A Lee, Ka-Ho %A Kai San Tse, Sunny %A Chan, Ka Wing %A Lin, Zhenyang %A Jia, Guochen %D 2015 %T Ruthenium-Catalyzed Deuteration of Alcohols with Deuterium Oxide %U https://acs.figshare.com/articles/dataset/Ruthenium_Catalyzed_Deuteration_of_Alcohols_with_Deuterium_Oxide/2202496 %R 10.1021/acs.organomet.5b00134.s002 %2 https://acs.figshare.com/ndownloader/files/3837052 %K octahedral ruthenium complexes %K D 2O %K NH %K cymene %K hydride species %K ruthenium hydride intermediates %K ruthenium complexes %K 2CH %X The catalytic properties of a series of ruthenium complexes for H/D exchange between D2O and alcohols were studied. The catalytic activity of the ruthenium complexes and the regioselectivity of the H/D exchange reactions were found to be dependent on the auxiliary ligands. While ruthenium η6-cymene complexes such as [(η6-cymene)­RuCl­(NH2CH2CH2NTs)]­Cl, (η6-cymene)­RuCl2/NH2CH2CH2OH, and (η6-cymene)­Ru­{(S,S)-NHCHPhCHPhNTs} catalyzed regioselective deuteration of alcohols with D2O at the β-carbon positions only, octahedral ruthenium complexes such as RuCl2(2-NH2CH2Py)­(PPh3)2 (2-NH2CH2Py = 2-aminomethylpyridine) and RuCl2(NH2CH2CH2NH2)­(PPh3)2 catalyzed regioselective H/D exchange reactions of D2O with alcohols at both the α- and β-carbon positions of alcohols. The H/D exchange reactions proceed through reversible dehydrogenation of alcohols and hydrogenation of carbonyl compounds involving hydride species and H/D exchange among D2O and carbonyl and hydride species. The different regioselectivities of the H/D exchange reactions can be related to the relative ease of H/D exchange of ruthenium hydride intermediates with D2O. %I ACS Publications