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Development of Imine Derivative Ligands for the Exocyclic Activation of Late Transition Metal Polymerization Catalysts

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Olefin Upgrading Catalysis by Nitrogen-based Metal Complexes II

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 36))

Abstract

Transition metal complexes bearing imine and imine derivative ligands represent a growing number of polymerization catalysts in development. The ease of synthesis and large number of structural variations which are readily accessible make these systems of great interest both academically and industrially. One subset of imine-based complexes are those which bear exocyclic functionality which can interact with Lewis acids. These systems are particularly interesting as the activation of the complex occurs remotely, away from the active center, and that the activation can proceed using stoichiometric concentrations of activators. In addition, the presence of the exocyclic functionality may present an effective method to heterogenize polymerization catalysts. In this chapter, the development of such systems and in particular ?-iminocarboxamide nickel catalysts and derivative species are discussed.

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Notes

  1. 1.

    Keep in consideration that solvent effects can greatly change the chemical shifts of these groups and in particular the protons associated with the imine/alcohol, however, the absolute trend should remain consistent.

  2. 2.

    A “better” ligand is normally one which is more compatible with the metal cation, as described by the hardness/softness of the metal and the ligand. Particularly, those which are multidentate ligands.

Abbreviations

Acac:

Acetylacetone

Ar:

Aryl

ArF:

Aryl group containing fluoro-atoms

B:

Lewis base

BCF:

Tris(pentafluorophenyl)borane

bipy:

2,2?-Bipyridyl

Bz:

Benzyl

Cn :

Complex

COD:

1,5-Cyclooctadiene

Dipp:

Diisopropylphenyl

dme:

Dimetoxiethane (ethylene glycol dimethylether)

en:

1,2-Diaminoethane

Et:

Ethyl

Ln :

Ligand

Ls :

Ligand salt

Lut:

Lutidine (2,6-dimethyl pyridine)

M:

Metal

MAO:

Methylaluminoxane

Me:

Methyl

NacNacH:

1,3-Diketimines

Px :

Metal precursor

Ph:

Phenyl

Py:

Pyridine

r.t.:

Room temperature

THF:

Tetrahydrofuran

Ts-CN:

Para-toluenesulfonylcyanide

tmeda:

N,N,N?,N?-tetramethylethylenediamine

X:

Halogen or other anionic group

Y:

Alkyl or functional groups

Z?Z?:

Bidentate ligand (where Z is the coordinating atom)

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Acknowledgments

The authors wish to acknowledge the kind assistance of M. Valderrama, V. Dougnac and M. Deij in the preparation of this work. New x-ray structures were supplied via collaboration with Professors G. Erker and R. Frölich (Organisch-Chemisches Institut, Universtät Münster). Partial funding was provided through FONDECYT 1100286 and the Alexander von Humboldt Foundation.

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  1. Departamento de Ingeniería Química, Centro para la Investigación Interdisciplinaria Avanzada en Ciencias de los Materiales (CIMAT), Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Santiago, Chile

    Brian C. Peoples

  2. Departamento de Química Inorgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago, Chile

    René S. Rojas

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  1. Brian C. Peoples
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  2. René S. Rojas
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Correspondence to René S. Rojas .

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  1. CSIC-Universidad de Sevilla., Instituto de Investigaciones Químicas, C/ Americo Vespucio 49, Sevilla, 41092, Spain

    Juan CAMPORA

  2. ICCOM, Florence research area, National Council of Research - CNR, Via Madonna del Piano 10, Florence, 50019, Italy

    Giuliano GIAMBASTIANI

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Peoples, B.C., Rojas, R.S. (2011). Development of Imine Derivative Ligands for the Exocyclic Activation of Late Transition Metal Polymerization Catalysts. In: CAMPORA, J., GIAMBASTIANI, G. (eds) Olefin Upgrading Catalysis by Nitrogen-based Metal Complexes II. Catalysis by Metal Complexes, vol 36. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0696-5_2

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