A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions

Ole H. Winkelmann; Andrei Riekstins; Steven P. Nolan; Oscar Navarro

doi:10.1021/om900677v

A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions

Ole H. Winkelmann, Andrei Riekstins, Steven P. Nolan, Oscar Navarro

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

67 Citations (Scopus)

Abstract

The synthesis of the new well-defined and air-stable complex (SIPr)Pd(acac)Cl (SIPr = 1,3-bis(2,6-diisopropylpheiiyl)imidazolin-2-ylidene) is described, and the catalytic activity of this new complex has been tested in the alpha-arylation of ketones and in Buchwald-Hartwig amination reactions. The significant differences in catalytic performance when compared to the previously reported, unsaturated counterpart (IPr)Pd(acac)Cl (IPr = 1,3-bis(2,6-diisopropylplienyl)imidazol-2-ylidene) are discussed by means of X-ray crystallography and on the basis of their varying solution dynamics, observed by H-1 NMR spectroscopy.

Original language	English
Pages (from-to)	5809-5813
Number of pages	5
Journal	Organometallics
Volume	28
Issue number	19
DOIs	https://doi.org/10.1021/om900677v
Publication status	Published - 12 Oct 2009

Keywords

OLEFIN METATHESIS
ELECTRONIC-PROPERTIES
(NHC)PD(ALLYL)CL NHC
PALLADIUM COMPLEXES
TRANSITION-METALS
LIGANDS
CATALYSTS
EFFICIENT

Access to Document

10.1021/om900677v

Cite this

@article{8002726e19e2456499a48f50955d6e90,

title = "A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions",

abstract = "The synthesis of the new well-defined and air-stable complex (SIPr)Pd(acac)Cl (SIPr = 1,3-bis(2,6-diisopropylpheiiyl)imidazolin-2-ylidene) is described, and the catalytic activity of this new complex has been tested in the alpha-arylation of ketones and in Buchwald-Hartwig amination reactions. The significant differences in catalytic performance when compared to the previously reported, unsaturated counterpart (IPr)Pd(acac)Cl (IPr = 1,3-bis(2,6-diisopropylplienyl)imidazol-2-ylidene) are discussed by means of X-ray crystallography and on the basis of their varying solution dynamics, observed by H-1 NMR spectroscopy.",

keywords = "OLEFIN METATHESIS, ELECTRONIC-PROPERTIES, (NHC)PD(ALLYL)CL NHC, PALLADIUM COMPLEXES, TRANSITION-METALS, LIGANDS, CATALYSTS, EFFICIENT",

author = "Winkelmann, {Ole H.} and Andrei Riekstins and Nolan, {Steven P.} and Oscar Navarro",

year = "2009",

month = oct,

day = "12",

doi = "10.1021/om900677v",

language = "English",

volume = "28",

pages = "5809--5813",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "19",

}

A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions. / Winkelmann, Ole H.; Riekstins, Andrei; Nolan, Steven P. et al.
In: Organometallics, Vol. 28, No. 19, 12.10.2009, p. 5809-5813.

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

TY - JOUR

T1 - A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions

AU - Winkelmann, Ole H.

AU - Riekstins, Andrei

AU - Nolan, Steven P.

AU - Navarro, Oscar

PY - 2009/10/12

Y1 - 2009/10/12

N2 - The synthesis of the new well-defined and air-stable complex (SIPr)Pd(acac)Cl (SIPr = 1,3-bis(2,6-diisopropylpheiiyl)imidazolin-2-ylidene) is described, and the catalytic activity of this new complex has been tested in the alpha-arylation of ketones and in Buchwald-Hartwig amination reactions. The significant differences in catalytic performance when compared to the previously reported, unsaturated counterpart (IPr)Pd(acac)Cl (IPr = 1,3-bis(2,6-diisopropylplienyl)imidazol-2-ylidene) are discussed by means of X-ray crystallography and on the basis of their varying solution dynamics, observed by H-1 NMR spectroscopy.

AB - The synthesis of the new well-defined and air-stable complex (SIPr)Pd(acac)Cl (SIPr = 1,3-bis(2,6-diisopropylpheiiyl)imidazolin-2-ylidene) is described, and the catalytic activity of this new complex has been tested in the alpha-arylation of ketones and in Buchwald-Hartwig amination reactions. The significant differences in catalytic performance when compared to the previously reported, unsaturated counterpart (IPr)Pd(acac)Cl (IPr = 1,3-bis(2,6-diisopropylplienyl)imidazol-2-ylidene) are discussed by means of X-ray crystallography and on the basis of their varying solution dynamics, observed by H-1 NMR spectroscopy.

KW - OLEFIN METATHESIS

KW - ELECTRONIC-PROPERTIES

KW - (NHC)PD(ALLYL)CL NHC

KW - PALLADIUM COMPLEXES

KW - TRANSITION-METALS

KW - LIGANDS

KW - CATALYSTS

KW - EFFICIENT

UR - http://www.scopus.com/inward/record.url?scp=70349777583&partnerID=8YFLogxK

U2 - 10.1021/om900677v

DO - 10.1021/om900677v

M3 - Article

SN - 0276-7333

VL - 28

SP - 5809

EP - 5813

JO - Organometallics

JF - Organometallics

IS - 19

ER -

A Comparative Study on (NHC)Pd(acac)Cl Complexes (NHC = N-heterocyclic carbene): Indications for the Origin of the Different Reactivity of Saturated and Unsaturated NHC in Cross-Coupling Reactions

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this