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Ruthenium-Catalyzed Deuteration of Alcohols with Deuterium Oxide

Authors Bai, Wei HKUST affiliated (currently or previously)
Lee, Kaho HKUST affiliated (currently or previously)
Tse, Sunny Kai San HKUST affiliated (currently or previously)
Chan, Ka Wing HKUST affiliated (currently or previously)
Lin, Zhenyang View this author's profile
Jia, Guochen View this author's profile
Issue Date 2015
Source Organometallics , v. 34, (15), August 2015, p. 3686-3698
Summary 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 eta(6)-cymene complexes such as cymene)RuCl(NH2CH2CH2NTs)]Cl, (eta(6)-cymene)RuCl2/ NH2CH2CH2OH, and (eta(6)-cymene)Ru{(S,S)-NHCHPhCHPhNTs} catalyzed regioselective deuteration of alcohols with D2O at the beta-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 alpha- and beta-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.
ISSN 0276-7333
Language English
Format Article
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