Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines

Masato Ito; Makoto Hirakawa; Kunihiko Murata; Takao Ikariya

doi:10.1021/om000912+

Hydrogenation of aromatic ketones catalyzed by (η⁵-C₅(CH₃)₅)Ru complexes bearing primary amines

Masato Ito, Makoto Hirakawa, Kunihiko Murata, Takao Ikariya

Research output: Contribution to journal › Article › peer-review

170 Citations (Scopus)

Abstract

The rapid hydrogenation of simple aromatic ketones is accomplished by using a combination of (η⁵-C₅(CH₃)₅)Ru complexes and primary amines as a catalyst in 2-propanol. In particular, 1,2-diamines with primary and tertiary amino groups at both ends exhibit a significant ligand acceleration effect. Isotope-labeling experiments using D₂ and 2-propanol-d_n reveal that 2-propanol participates in the activation of H₂ based on a metal/NH bifunctional effect to facilitate the hydrogenation. Asymmetric hydrogenation of prochiral simple ketones with the chiral version of the catalysts provides optically active secondary alcohols with up to 95% ee.

Original language	English
Pages (from-to)	379-381
Number of pages	3
Journal	Organometallics
Volume	20
Issue number	3
DOIs	https://doi.org/10.1021/om000912+
Publication status	Published - Feb 5 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The rapid hydrogenation of simple aromatic ketones is accomplished by using a combination of (η5-C5(CH3)5)Ru complexes and primary amines as a catalyst in 2-propanol. In particular, 1,2-diamines with primary and tertiary amino groups at both ends exhibit a significant ligand acceleration effect. Isotope-labeling experiments using D2 and 2-propanol-dn reveal that 2-propanol participates in the activation of H2 based on a metal/NH bifunctional effect to facilitate the hydrogenation. Asymmetric hydrogenation of prochiral simple ketones with the chiral version of the catalysts provides optically active secondary alcohols with up to 95% ee.",

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T1 - Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines

AU - Ito, Masato

AU - Hirakawa, Makoto

AU - Murata, Kunihiko

AU - Ikariya, Takao

PY - 2001/2/5

Y1 - 2001/2/5

N2 - The rapid hydrogenation of simple aromatic ketones is accomplished by using a combination of (η5-C5(CH3)5)Ru complexes and primary amines as a catalyst in 2-propanol. In particular, 1,2-diamines with primary and tertiary amino groups at both ends exhibit a significant ligand acceleration effect. Isotope-labeling experiments using D2 and 2-propanol-dn reveal that 2-propanol participates in the activation of H2 based on a metal/NH bifunctional effect to facilitate the hydrogenation. Asymmetric hydrogenation of prochiral simple ketones with the chiral version of the catalysts provides optically active secondary alcohols with up to 95% ee.

AB - The rapid hydrogenation of simple aromatic ketones is accomplished by using a combination of (η5-C5(CH3)5)Ru complexes and primary amines as a catalyst in 2-propanol. In particular, 1,2-diamines with primary and tertiary amino groups at both ends exhibit a significant ligand acceleration effect. Isotope-labeling experiments using D2 and 2-propanol-dn reveal that 2-propanol participates in the activation of H2 based on a metal/NH bifunctional effect to facilitate the hydrogenation. Asymmetric hydrogenation of prochiral simple ketones with the chiral version of the catalysts provides optically active secondary alcohols with up to 95% ee.

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Hydrogenation of aromatic ketones catalyzed by (η⁵-C₅(CH₃)₅)Ru complexes bearing primary amines

Abstract

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