Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

Mihai S. Viciu; Oscar Navarro; Romain F. Germaneau; Roy A. Kelly; William Sommer; Nicolas Marion; Erwin D. Stevens; Luigi Cavallo; Steven P. Nolan

doi:10.1021/om034319e

Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

Mihai S. Viciu, Oscar Navarro, Romain F. Germaneau, Roy A. Kelly, William Sommer, Nicolas Marion, Erwin D. Stevens, Luigi Cavallo, Steven P. Nolan^*

^*Corresponding author for this work

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

293 Scopus citations

Abstract

The synthesis and structural characterization of a series of palladium complexes bearing N-heterocyclic carbenes (NHC) as supporting ligands are described. The reaction of commercially available [Pd(allyl)Cl]₂ and isolated or in situ generated NHC leads to monomeric palladium complexes where one NHC is bound to the metal center, as indicated by spectroscopic and single-crystal X-ray diffraction studies. The relative reactivity trend for these complexes as catalysts in aryl amination is discussed in terms of ligand steric properties, which vary as a function of imidazole-nitrogen substituents and perturbation resulting in modulation of ring planarity. The concept of buried volume is used to quantify the steric demand of each NHC in the corresponding complexes.

Original language	English (US)
Pages (from-to)	1629-1635
Number of pages	7
Journal	Organometallics
Volume	23
Issue number	7
DOIs	https://doi.org/10.1021/om034319e
State	Published - Mar 29 2004
Externally published	Yes

ASJC Scopus subject areas

Inorganic Chemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)",

abstract = "The synthesis and structural characterization of a series of palladium complexes bearing N-heterocyclic carbenes (NHC) as supporting ligands are described. The reaction of commercially available [Pd(allyl)Cl]2 and isolated or in situ generated NHC leads to monomeric palladium complexes where one NHC is bound to the metal center, as indicated by spectroscopic and single-crystal X-ray diffraction studies. The relative reactivity trend for these complexes as catalysts in aryl amination is discussed in terms of ligand steric properties, which vary as a function of imidazole-nitrogen substituents and perturbation resulting in modulation of ring planarity. The concept of buried volume is used to quantify the steric demand of each NHC in the corresponding complexes.",

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language = "English (US)",

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T1 - Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

AU - Viciu, Mihai S.

AU - Navarro, Oscar

AU - Germaneau, Romain F.

AU - Kelly, Roy A.

AU - Sommer, William

AU - Marion, Nicolas

AU - Stevens, Erwin D.

AU - Cavallo, Luigi

AU - Nolan, Steven P.

PY - 2004/3/29

Y1 - 2004/3/29

N2 - The synthesis and structural characterization of a series of palladium complexes bearing N-heterocyclic carbenes (NHC) as supporting ligands are described. The reaction of commercially available [Pd(allyl)Cl]2 and isolated or in situ generated NHC leads to monomeric palladium complexes where one NHC is bound to the metal center, as indicated by spectroscopic and single-crystal X-ray diffraction studies. The relative reactivity trend for these complexes as catalysts in aryl amination is discussed in terms of ligand steric properties, which vary as a function of imidazole-nitrogen substituents and perturbation resulting in modulation of ring planarity. The concept of buried volume is used to quantify the steric demand of each NHC in the corresponding complexes.

AB - The synthesis and structural characterization of a series of palladium complexes bearing N-heterocyclic carbenes (NHC) as supporting ligands are described. The reaction of commercially available [Pd(allyl)Cl]2 and isolated or in situ generated NHC leads to monomeric palladium complexes where one NHC is bound to the metal center, as indicated by spectroscopic and single-crystal X-ray diffraction studies. The relative reactivity trend for these complexes as catalysts in aryl amination is discussed in terms of ligand steric properties, which vary as a function of imidazole-nitrogen substituents and perturbation resulting in modulation of ring planarity. The concept of buried volume is used to quantify the steric demand of each NHC in the corresponding complexes.

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U2 - 10.1021/om034319e

DO - 10.1021/om034319e

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JO - Organometallics

JF - Organometallics

IS - 7

ER -

Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

Abstract

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