Abnormal N-heterocyclic carbene-phosphine ruthenium(II) complexes as active catalysts for transfer hydrogenation

Julia Witt; Alexander Pöthig; Fritz E. Kühn; Walter Baratta

doi:10.1021/om400400w

Abnormal N-heterocyclic carbene-phosphine ruthenium(II) complexes as active catalysts for transfer hydrogenation

Julia Witt
, Alexander Pöthig
, Fritz E. Kühn
, Walter Baratta

Associate Professorship of Molecular Catalysis

Technical University of Munich
Università degli Studi di Udine

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

62 Scopus citations

Abstract

The bifunctional phosphine-abnormal N-heterocyclic carbene ruthenium(II) complex RuBr(OAc)(PPh₃)(P-aNHC) (1) has been synthesized in high yield by reaction of Ru(OAc)₂(PPh₃)₂ with a phosphine imidazolium bromide (P-NHC × HBr) and characterized by X-ray diffraction. This compound shows high catalytic activity for the transfer hydrogenation of ketones to alcohols in 2-propanol. Rate and efficiency of 1 can be enhanced by the addition of ethylenediamine or benzylamine, affording TOFs up to 140 000 h^-1. Reaction of 1 with ethylenediamine leads to the Ru carbene/amine complex [Ru(OAc)(PPh₃)(P-aNHC)(H₂NCH ₂CH₂NH₂)]Br (2), which displays the same activity of the in situ generated species.

Original language	English
Pages (from-to)	4042-4045
Number of pages	4
Journal	Organometallics
Volume	32
Issue number	15
DOIs	https://doi.org/10.1021/om400400w
State	Published - 12 Aug 2013

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title = "Abnormal N-heterocyclic carbene-phosphine ruthenium(II) complexes as active catalysts for transfer hydrogenation",

abstract = "The bifunctional phosphine-abnormal N-heterocyclic carbene ruthenium(II) complex RuBr(OAc)(PPh3)(P-aNHC) (1) has been synthesized in high yield by reaction of Ru(OAc)2(PPh3)2 with a phosphine imidazolium bromide (P-NHC × HBr) and characterized by X-ray diffraction. This compound shows high catalytic activity for the transfer hydrogenation of ketones to alcohols in 2-propanol. Rate and efficiency of 1 can be enhanced by the addition of ethylenediamine or benzylamine, affording TOFs up to 140 000 h-1. Reaction of 1 with ethylenediamine leads to the Ru carbene/amine complex [Ru(OAc)(PPh3)(P-aNHC)(H2NCH 2CH2NH2)]Br (2), which displays the same activity of the in situ generated species.",

author = "Julia Witt and Alexander P{\"o}thig and K{\"u}hn, \{Fritz E.\} and Walter Baratta",

year = "2013",

month = aug,

day = "12",

doi = "10.1021/om400400w",

language = "English",

volume = "32",

pages = "4042--4045",

journal = "Organometallics",

issn = "0276-7333",

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TY - JOUR

T1 - Abnormal N-heterocyclic carbene-phosphine ruthenium(II) complexes as active catalysts for transfer hydrogenation

AU - Witt, Julia

AU - Pöthig, Alexander

AU - Kühn, Fritz E.

AU - Baratta, Walter

PY - 2013/8/12

Y1 - 2013/8/12

N2 - The bifunctional phosphine-abnormal N-heterocyclic carbene ruthenium(II) complex RuBr(OAc)(PPh3)(P-aNHC) (1) has been synthesized in high yield by reaction of Ru(OAc)2(PPh3)2 with a phosphine imidazolium bromide (P-NHC × HBr) and characterized by X-ray diffraction. This compound shows high catalytic activity for the transfer hydrogenation of ketones to alcohols in 2-propanol. Rate and efficiency of 1 can be enhanced by the addition of ethylenediamine or benzylamine, affording TOFs up to 140 000 h-1. Reaction of 1 with ethylenediamine leads to the Ru carbene/amine complex [Ru(OAc)(PPh3)(P-aNHC)(H2NCH 2CH2NH2)]Br (2), which displays the same activity of the in situ generated species.

AB - The bifunctional phosphine-abnormal N-heterocyclic carbene ruthenium(II) complex RuBr(OAc)(PPh3)(P-aNHC) (1) has been synthesized in high yield by reaction of Ru(OAc)2(PPh3)2 with a phosphine imidazolium bromide (P-NHC × HBr) and characterized by X-ray diffraction. This compound shows high catalytic activity for the transfer hydrogenation of ketones to alcohols in 2-propanol. Rate and efficiency of 1 can be enhanced by the addition of ethylenediamine or benzylamine, affording TOFs up to 140 000 h-1. Reaction of 1 with ethylenediamine leads to the Ru carbene/amine complex [Ru(OAc)(PPh3)(P-aNHC)(H2NCH 2CH2NH2)]Br (2), which displays the same activity of the in situ generated species.

UR - https://www.scopus.com/pages/publications/84881540234

U2 - 10.1021/om400400w

DO - 10.1021/om400400w

M3 - Article

AN - SCOPUS:84881540234

SN - 0276-7333

VL - 32

SP - 4042

EP - 4045

JO - Organometallics

JF - Organometallics

IS - 15

ER -

Abnormal N-heterocyclic carbene-phosphine ruthenium(II) complexes as active catalysts for transfer hydrogenation

Abstract

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