SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions

Ziyauddin Qureshi; Ali Imad Ali Hamieh; Samir Barman; Niladri Maity; Manoja Samantaray; Samy Ould-Chikh; Edy Abou-Hamad; Laura Falivene; Valerio D’Elia; Alexander Rothenberger; Isabelle Llorens; Jean-Louis Hazemann; Jean-Marie Basset

doi:10.1021/acs.inorgchem.6b02424

SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions

Ziyauddin Qureshi, Ali Imad Ali Hamieh, Samir Barman, Niladri Maity, Manoja Samantaray, Samy Ould-Chikh, Edy Abou-Hamad, Laura Falivene, Valerio D’Elia, Alexander Rothenberger, Isabelle Llorens, Jean-Louis Hazemann, Jean-Marie Basset

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Abstract

Synthesis, structure, and olefin metathesis activity of a surface complex [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4) (ImDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-iminato) supported on silica by a surface organometallic chemistry (SOMC) approach are reported. The reaction of N-silylated 2-iminoimidazoline with tungsten(VI) oxytetrachloride generated the tungsten oxo imidazolin-2-iminato chloride complex [ImDippNW(═O)Cl3] (2). This was grafted on partially dehydroxylated silica pretreated at 700 °C (SiO2-700) to afford a well-defined monopodal surface complex [(≡Si-O-)W(═O)Cl2-ImDippN] (3). 3 underwent alkylation by ZnMe2 to produce [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4). The alkylated surface complex was thoroughly characterized by solid-state NMR, elemental microanalysis, Raman, FT-IR spectroscopies, and XAS analysis. 4 proved to be an active precatalyst for self-metathesis of terminal olefins such as propylene and 1-hexene.

Original language	English (US)
Pages (from-to)	861-871
Number of pages	11
Journal	Inorganic Chemistry
Volume	56
Issue number	2
DOIs	https://doi.org/10.1021/acs.inorgchem.6b02424
State	Published - Jan 5 2017

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Qureshi, Z., Hamieh, A. I. A., Barman, S., Maity, N., Samantaray, M., Ould-Chikh, S., Abou-Hamad, E., Falivene, L., D’Elia, V., Rothenberger, A., Llorens, I., Hazemann, J.-L., & Basset, J.-M. (2017). SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions. Inorganic Chemistry, 56(2), 861-871. https://doi.org/10.1021/acs.inorgchem.6b02424

@article{53a9525ef21f406f9bd831e80668a681,

title = "SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions",

abstract = "Synthesis, structure, and olefin metathesis activity of a surface complex [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4) (ImDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-iminato) supported on silica by a surface organometallic chemistry (SOMC) approach are reported. The reaction of N-silylated 2-iminoimidazoline with tungsten(VI) oxytetrachloride generated the tungsten oxo imidazolin-2-iminato chloride complex [ImDippNW(═O)Cl3] (2). This was grafted on partially dehydroxylated silica pretreated at 700 °C (SiO2-700) to afford a well-defined monopodal surface complex [(≡Si-O-)W(═O)Cl2-ImDippN] (3). 3 underwent alkylation by ZnMe2 to produce [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4). The alkylated surface complex was thoroughly characterized by solid-state NMR, elemental microanalysis, Raman, FT-IR spectroscopies, and XAS analysis. 4 proved to be an active precatalyst for self-metathesis of terminal olefins such as propylene and 1-hexene.",

author = "Ziyauddin Qureshi and Hamieh, {Ali Imad Ali} and Samir Barman and Niladri Maity and Manoja Samantaray and Samy Ould-Chikh and Edy Abou-Hamad and Laura Falivene and Valerio D{\textquoteright}Elia and Alexander Rothenberger and Isabelle Llorens and Jean-Louis Hazemann and Jean-Marie Basset",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).",

year = "2017",

month = jan,

day = "5",

doi = "10.1021/acs.inorgchem.6b02424",

language = "English (US)",

volume = "56",

pages = "861--871",

journal = "Inorganic Chemistry",

issn = "0020-1669",

publisher = "American Chemical Society",

number = "2",

}

Qureshi, Z, Hamieh, AIA, Barman, S, Maity, N, Samantaray, M, Ould-Chikh, S, Abou-Hamad, E, Falivene, L, D’Elia, V, Rothenberger, A, Llorens, I, Hazemann, J-L & Basset, J-M 2017, 'SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions', Inorganic Chemistry, vol. 56, no. 2, pp. 861-871. https://doi.org/10.1021/acs.inorgchem.6b02424

TY - JOUR

T1 - SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions

AU - Qureshi, Ziyauddin

AU - Hamieh, Ali Imad Ali

AU - Barman, Samir

AU - Maity, Niladri

AU - Samantaray, Manoja

AU - Ould-Chikh, Samy

AU - Abou-Hamad, Edy

AU - Falivene, Laura

AU - D’Elia, Valerio

AU - Rothenberger, Alexander

AU - Llorens, Isabelle

AU - Hazemann, Jean-Louis

AU - Basset, Jean-Marie

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).

PY - 2017/1/5

Y1 - 2017/1/5

N2 - Synthesis, structure, and olefin metathesis activity of a surface complex [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4) (ImDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-iminato) supported on silica by a surface organometallic chemistry (SOMC) approach are reported. The reaction of N-silylated 2-iminoimidazoline with tungsten(VI) oxytetrachloride generated the tungsten oxo imidazolin-2-iminato chloride complex [ImDippNW(═O)Cl3] (2). This was grafted on partially dehydroxylated silica pretreated at 700 °C (SiO2-700) to afford a well-defined monopodal surface complex [(≡Si-O-)W(═O)Cl2-ImDippN] (3). 3 underwent alkylation by ZnMe2 to produce [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4). The alkylated surface complex was thoroughly characterized by solid-state NMR, elemental microanalysis, Raman, FT-IR spectroscopies, and XAS analysis. 4 proved to be an active precatalyst for self-metathesis of terminal olefins such as propylene and 1-hexene.

AB - Synthesis, structure, and olefin metathesis activity of a surface complex [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4) (ImDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-iminato) supported on silica by a surface organometallic chemistry (SOMC) approach are reported. The reaction of N-silylated 2-iminoimidazoline with tungsten(VI) oxytetrachloride generated the tungsten oxo imidazolin-2-iminato chloride complex [ImDippNW(═O)Cl3] (2). This was grafted on partially dehydroxylated silica pretreated at 700 °C (SiO2-700) to afford a well-defined monopodal surface complex [(≡Si-O-)W(═O)Cl2-ImDippN] (3). 3 underwent alkylation by ZnMe2 to produce [(≡Si-O-)W(═O)(CH3)2-ImDippN] (4). The alkylated surface complex was thoroughly characterized by solid-state NMR, elemental microanalysis, Raman, FT-IR spectroscopies, and XAS analysis. 4 proved to be an active precatalyst for self-metathesis of terminal olefins such as propylene and 1-hexene.

UR - http://hdl.handle.net/10754/622794

UR - http://pubs.acs.org/doi/full/10.1021/acs.inorgchem.6b02424

UR - http://www.scopus.com/inward/record.url?scp=85009773789&partnerID=8YFLogxK

U2 - 10.1021/acs.inorgchem.6b02424

DO - 10.1021/acs.inorgchem.6b02424

M3 - Article

C2 - 28055202

SN - 0020-1669

VL - 56

SP - 861

EP - 871

JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 2

ER -

SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions

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CCDC 1501262: Experimental Crystal Structure Determination : (1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-iminato)-trichloro-oxo-tungsten dichloromethane solvate

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SOMC-Designed Silica Supported Tungsten Oxo Imidazolin-2-iminato Methyl Precatalyst for Olefin Metathesis Reactions

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CCDC 1501262: Experimental Crystal Structure Determination : (1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-iminato)-trichloro-oxo-tungsten dichloromethane solvate

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