2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

Makoto Muranaka; Isao Hyodo; Wataru Okumura; Toshiyuki Oshiki

doi:10.1016/j.cattod.2010.11.050

2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

Makoto Muranaka, Isao Hyodo, Wataru Okumura, Toshiyuki Oshiki

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

37 Citations (Scopus)

Abstract

New homogeneous catalyst comprised of [Ru(methallyl)₂(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl)amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 °C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of byproducts. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically.

Original language	English
Pages (from-to)	552-555
Number of pages	4
Journal	Catalysis Today
Volume	164
Issue number	1
DOIs	https://doi.org/10.1016/j.cattod.2010.11.050
Publication status	Published - Apr 30 2011

Keywords

Amides
Homogeneous catalysis
Hydration
Nitrile
Phosphine
Ruthenium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1016/j.cattod.2010.11.050

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@article{5495046b9aac4f9e9a77fbd7b36ad66c,

title = "2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions",

abstract = "New homogeneous catalyst comprised of [Ru(methallyl)2(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl)amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 °C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of byproducts. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically.",

keywords = "Amides, Homogeneous catalysis, Hydration, Nitrile, Phosphine, Ruthenium",

author = "Makoto Muranaka and Isao Hyodo and Wataru Okumura and Toshiyuki Oshiki",

note = "Funding Information: We thank ZEON Corporation for a generous gift of commercial cyclopentyl methyl ether. This work was supported by the JST-project to develop “innovative seeds” and an Industrial Technology Research Grant Program in 2006 from NEDO of Japan . ",

year = "2011",

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doi = "10.1016/j.cattod.2010.11.050",

language = "English",

volume = "164",

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journal = "Catalysis Today",

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T1 - 2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

AU - Muranaka, Makoto

AU - Hyodo, Isao

AU - Okumura, Wataru

AU - Oshiki, Toshiyuki

N1 - Funding Information: We thank ZEON Corporation for a generous gift of commercial cyclopentyl methyl ether. This work was supported by the JST-project to develop “innovative seeds” and an Industrial Technology Research Grant Program in 2006 from NEDO of Japan .

PY - 2011/4/30

Y1 - 2011/4/30

N2 - New homogeneous catalyst comprised of [Ru(methallyl)2(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl)amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 °C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of byproducts. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically.

AB - New homogeneous catalyst comprised of [Ru(methallyl)2(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl)amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 °C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of byproducts. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically.

KW - Amides

KW - Homogeneous catalysis

KW - Hydration

KW - Nitrile

KW - Phosphine

KW - Ruthenium

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U2 - 10.1016/j.cattod.2010.11.050

DO - 10.1016/j.cattod.2010.11.050

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JO - Catalysis Today

JF - Catalysis Today

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ER -

2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

Abstract

Keywords

ASJC Scopus subject areas

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