A stable crystalline imino-N-heterocyclic carbene ligand and its corresponding palladium(II) and rhodium(I) complexes

Sarim Dastgir; Karl S. Coleman; Andrew R. Cowley; Malcolm L.H. Green

doi:10.1021/om050775m

A stable crystalline imino-N-heterocyclic carbene ligand and its corresponding palladium(II) and rhodium(I) complexes

Sarim Dastgir, Karl S. Coleman^*, Andrew R. Cowley, Malcolm L.H. Green

^*Corresponding author for this work

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

77 Citations (Scopus)

Abstract

The crystalline heteroditopic, acyclic, and nonenolizable imino-N-heterocyclic carbene chelating ligand 1-tert-butyl-3-(1- phenyliminophenylmethylene)imidazol-2-ylidene (designated as CAimine) has been isolated and structurally characterized. The metal complexes [Pd(CAimine)Cl ₂], [Pd(allyl)(CAimine)]-PF₆, [Rh(COD)(CAimine)]PF ₆, and [Rh(CO)(CAimine)₂]Cl have been prepared either by Ag transfer or by reaction with the free carbene. The palladium(II) complexes have been tested for catalytic application in Suzuki type C-C cross-coupling reactions of aryl bromides and the rhodium(I) complexes for the catalytic hydroformylation of 1-octene. The metal complexes [Pd(CAimine)Cl₂], [Pd(allyl)(CAimine)]-PF₆, and [Rh(CO)(CAimine)₂]Cl have been structurally characterized by single-crystal X-ray diffraction.

Original language	English
Pages (from-to)	300-306
Number of pages	7
Journal	Organometallics
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/om050775m
Publication status	Published - 2 Jan 2006
Externally published	Yes

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title = "A stable crystalline imino-N-heterocyclic carbene ligand and its corresponding palladium(II) and rhodium(I) complexes",

abstract = "The crystalline heteroditopic, acyclic, and nonenolizable imino-N-heterocyclic carbene chelating ligand 1-tert-butyl-3-(1- phenyliminophenylmethylene)imidazol-2-ylidene (designated as CAimine) has been isolated and structurally characterized. The metal complexes [Pd(CAimine)Cl 2], [Pd(allyl)(CAimine)]-PF6, [Rh(COD)(CAimine)]PF 6, and [Rh(CO)(CAimine)2]Cl have been prepared either by Ag transfer or by reaction with the free carbene. The palladium(II) complexes have been tested for catalytic application in Suzuki type C-C cross-coupling reactions of aryl bromides and the rhodium(I) complexes for the catalytic hydroformylation of 1-octene. The metal complexes [Pd(CAimine)Cl2], [Pd(allyl)(CAimine)]-PF6, and [Rh(CO)(CAimine)2]Cl have been structurally characterized by single-crystal X-ray diffraction.",

author = "Sarim Dastgir and Coleman, {Karl S.} and Cowley, {Andrew R.} and Green, {Malcolm L.H.}",

year = "2006",

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doi = "10.1021/om050775m",

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T1 - A stable crystalline imino-N-heterocyclic carbene ligand and its corresponding palladium(II) and rhodium(I) complexes

AU - Dastgir, Sarim

AU - Coleman, Karl S.

AU - Cowley, Andrew R.

AU - Green, Malcolm L.H.

PY - 2006/1/2

Y1 - 2006/1/2

N2 - The crystalline heteroditopic, acyclic, and nonenolizable imino-N-heterocyclic carbene chelating ligand 1-tert-butyl-3-(1- phenyliminophenylmethylene)imidazol-2-ylidene (designated as CAimine) has been isolated and structurally characterized. The metal complexes [Pd(CAimine)Cl 2], [Pd(allyl)(CAimine)]-PF6, [Rh(COD)(CAimine)]PF 6, and [Rh(CO)(CAimine)2]Cl have been prepared either by Ag transfer or by reaction with the free carbene. The palladium(II) complexes have been tested for catalytic application in Suzuki type C-C cross-coupling reactions of aryl bromides and the rhodium(I) complexes for the catalytic hydroformylation of 1-octene. The metal complexes [Pd(CAimine)Cl2], [Pd(allyl)(CAimine)]-PF6, and [Rh(CO)(CAimine)2]Cl have been structurally characterized by single-crystal X-ray diffraction.

AB - The crystalline heteroditopic, acyclic, and nonenolizable imino-N-heterocyclic carbene chelating ligand 1-tert-butyl-3-(1- phenyliminophenylmethylene)imidazol-2-ylidene (designated as CAimine) has been isolated and structurally characterized. The metal complexes [Pd(CAimine)Cl 2], [Pd(allyl)(CAimine)]-PF6, [Rh(COD)(CAimine)]PF 6, and [Rh(CO)(CAimine)2]Cl have been prepared either by Ag transfer or by reaction with the free carbene. The palladium(II) complexes have been tested for catalytic application in Suzuki type C-C cross-coupling reactions of aryl bromides and the rhodium(I) complexes for the catalytic hydroformylation of 1-octene. The metal complexes [Pd(CAimine)Cl2], [Pd(allyl)(CAimine)]-PF6, and [Rh(CO)(CAimine)2]Cl have been structurally characterized by single-crystal X-ray diffraction.

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DO - 10.1021/om050775m

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JO - Organometallics

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IS - 1

ER -

A stable crystalline imino-N-heterocyclic carbene ligand and its corresponding palladium(II) and rhodium(I) complexes

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