Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation

Daniela A. Hey; Michael J. Sauer; Pauline J. Fischer; Eva Maria H.J. Esslinger; Fritz E. Kühn; Walter Baratta

doi:10.1002/cctc.202000542

Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation

Daniela A. Hey, Michael J. Sauer, Pauline J. Fischer, Eva Maria H.J. Esslinger, Fritz E. Kühn, Walter Baratta

Associate Professorship of Molecular Catalysis

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

15 Scopus citations

Abstract

The mixed acetate acetylacetonate (acac) ruthenium(II) phosphine complexes Ru(OAc)(acac)P₂ [P₂=(PPh₃)₂, Ph₂P(CH₂)₄PPh₂ (dppb)] were prepared by protonation of Ru(OAc)₂(PPh₃)₂ with acetylacetone in dichloromethane. Reaction of the dppb derivative with 2-(aminomethyl)pyridine (ampy) affords the complex Ru(OAc)(acac)(ampy)(dppb), which converts to [Ru(acac)(ampy)(dppb)](OAc) in toluene at 90 °C. In the former derivative the ampy ligand is monodentate and coordinates through the NH₂-moiety. The isolated acac complexes are active catalysts for the transfer hydrogenation of ketones with loadings as low as 0.01 mol%, the ampy having a strong accelerating effect. Several aromatic and aliphatic ketone substrates are converted to their corresponding alcohols, and different electronic influences through substituents on acetophenone are tolerated.

Original language	English
Pages (from-to)	3537-3544
Number of pages	8
Journal	ChemCatChem
Volume	12
Issue number	13
DOIs	https://doi.org/10.1002/cctc.202000542
State	Published - 6 Jul 2020

Keywords

2-(aminomethyl)pyridine
acetylacetonate
hydrogenation
ruthenium complexes
transfer hydrogenation

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title = "Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation",

abstract = "The mixed acetate acetylacetonate (acac) ruthenium(II) phosphine complexes Ru(OAc)(acac)P2 [P2=(PPh3)2, Ph2P(CH2)4PPh2 (dppb)] were prepared by protonation of Ru(OAc)2(PPh3)2 with acetylacetone in dichloromethane. Reaction of the dppb derivative with 2-(aminomethyl)pyridine (ampy) affords the complex Ru(OAc)(acac)(ampy)(dppb), which converts to [Ru(acac)(ampy)(dppb)](OAc) in toluene at 90 °C. In the former derivative the ampy ligand is monodentate and coordinates through the NH2-moiety. The isolated acac complexes are active catalysts for the transfer hydrogenation of ketones with loadings as low as 0.01 mol%, the ampy having a strong accelerating effect. Several aromatic and aliphatic ketone substrates are converted to their corresponding alcohols, and different electronic influences through substituents on acetophenone are tolerated.",

keywords = "2-(aminomethyl)pyridine, acetylacetonate, hydrogenation, ruthenium complexes, transfer hydrogenation",

author = "Hey, {Daniela A.} and Sauer, {Michael J.} and Fischer, {Pauline J.} and Esslinger, {Eva Maria H.J.} and K{\"u}hn, {Fritz E.} and Walter Baratta",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2020",

month = jul,

day = "6",

doi = "10.1002/cctc.202000542",

language = "English",

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T1 - Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation

AU - Hey, Daniela A.

AU - Sauer, Michael J.

AU - Fischer, Pauline J.

AU - Esslinger, Eva Maria H.J.

AU - Kühn, Fritz E.

AU - Baratta, Walter

PY - 2020/7/6

Y1 - 2020/7/6

N2 - The mixed acetate acetylacetonate (acac) ruthenium(II) phosphine complexes Ru(OAc)(acac)P2 [P2=(PPh3)2, Ph2P(CH2)4PPh2 (dppb)] were prepared by protonation of Ru(OAc)2(PPh3)2 with acetylacetone in dichloromethane. Reaction of the dppb derivative with 2-(aminomethyl)pyridine (ampy) affords the complex Ru(OAc)(acac)(ampy)(dppb), which converts to [Ru(acac)(ampy)(dppb)](OAc) in toluene at 90 °C. In the former derivative the ampy ligand is monodentate and coordinates through the NH2-moiety. The isolated acac complexes are active catalysts for the transfer hydrogenation of ketones with loadings as low as 0.01 mol%, the ampy having a strong accelerating effect. Several aromatic and aliphatic ketone substrates are converted to their corresponding alcohols, and different electronic influences through substituents on acetophenone are tolerated.

AB - The mixed acetate acetylacetonate (acac) ruthenium(II) phosphine complexes Ru(OAc)(acac)P2 [P2=(PPh3)2, Ph2P(CH2)4PPh2 (dppb)] were prepared by protonation of Ru(OAc)2(PPh3)2 with acetylacetone in dichloromethane. Reaction of the dppb derivative with 2-(aminomethyl)pyridine (ampy) affords the complex Ru(OAc)(acac)(ampy)(dppb), which converts to [Ru(acac)(ampy)(dppb)](OAc) in toluene at 90 °C. In the former derivative the ampy ligand is monodentate and coordinates through the NH2-moiety. The isolated acac complexes are active catalysts for the transfer hydrogenation of ketones with loadings as low as 0.01 mol%, the ampy having a strong accelerating effect. Several aromatic and aliphatic ketone substrates are converted to their corresponding alcohols, and different electronic influences through substituents on acetophenone are tolerated.

KW - 2-(aminomethyl)pyridine

KW - acetylacetonate

KW - hydrogenation

KW - ruthenium complexes

KW - transfer hydrogenation

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U2 - 10.1002/cctc.202000542

DO - 10.1002/cctc.202000542

M3 - Article

AN - SCOPUS:85085492118

SN - 1867-3880

VL - 12

SP - 3537

EP - 3544

JO - ChemCatChem

JF - ChemCatChem

IS - 13

ER -

Acetate Acetylacetonate Ampy Ruthenium(II) Complexes as Efficient Catalysts for Ketone Transfer Hydrogenation

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