Catalytic behavior of cationic hydridoruthenium(II) complex, [RuH(NH 3)(PMe3)4]+, in H 2-hydrogenation and transfer hydrogenation of imines

Yoshihito Kayaki, Hibiki Ikeda, Jun Ichirou Tsurumaki, Isao Shimizu, Akio Yamamoto

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)


Catalytic hydrogenation under H2 and transfer hydrogenation of imines by secondary alcohols with hydridoruthenium complexes bearing PMe 3 and PPh3 ligands have been examined. A cationic hydridoruthenium complex, cis-[RuH-(NH3)(PMe3) 4]PF6 (2), derived from cis-[RuH2(PMe 3)4] (1) and NH4PF6, showed higher catalytic activity for H2-hydrogenation of N-benzylideneaniline than neutral complexes such as 1 and cis- [RuClH(PMe3)4] (6). The effectiveness of cationic hydridoruthenium species for the catalytic H 2-hydrogenation of benzylideneaniline was also demonstrated by a marked increase in the yield of N-benzylaniline on treatment of 6 with AgPF 6. The cationic complex 2 was applicable to catalytic transfer hydrogenation of imines with secondary alcohols even in the absence of a base. Isotope labeling experiments using deuterated alcohols revealed that the hydrogen atom bound to the α-carbon of the donor alcohol was transferred exclusively to the imine carbon and alcoholic OD was transferred to the imine nitrogen. A rapid exchange between the alcoholic proton and the hydrido ligand of 2 was also confirmed by NMR investigation using (CH3) 2CHOD. On the basis of the experimental results the mechanisms of the H2-hydrogenation and transfer hydrogenation are discussed.

Original languageEnglish
Pages (from-to)1053-1061
Number of pages9
JournalBulletin of the Chemical Society of Japan
Issue number9
Publication statusPublished - 2008

ASJC Scopus subject areas

  • Chemistry(all)


Dive into the research topics of 'Catalytic behavior of cationic hydridoruthenium(II) complex, [RuH(NH <sub>3</sub>)(PMe<sub>3</sub>)<sub>4</sub>]<sup>+</sup>, in H <sub>2</sub>-hydrogenation and transfer hydrogenation of imines'. Together they form a unique fingerprint.

Cite this