Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

Mathieu Rouen; Pierre Queval; Laura Falivene; Jessica Allard; Loïc J. Toupet; Christophe Crévisy; Frédéric Caïjo; Olivier Baslé; Luigi Cavallo; Marc Mauduit

doi:10.1002/chem.201403934

Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

Mathieu Rouen, Pierre Queval, Laura Falivene, Jessica Allard, Loïc J. Toupet, Christophe Crévisy, Frédéric Caïjo, Olivier Baslé, Luigi Cavallo, Marc Mauduit

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

Abstract

An unexpected cationic bis-N-heterocyclic carbene (NHC) benzylidene ether based ruthenium complex (2 a) was prepared through the double incorporation of an unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligand that bore an N-substituted cyclododecyl side chain. The isolation and full characterization (including X-ray diffraction studies) of key synthetic intermediates along with theoretical calculations allowed us to understand the mechanism of the overall cationization process. Finally, the newly developed complex 2 a displayed interesting latent behavior during ring-closing metathesis, which could be "switched on" under acidic conditions.

Original language	English (US)
Pages (from-to)	13716-13721
Number of pages	6
Journal	Chemistry - A European Journal
Volume	20
Issue number	42
DOIs	https://doi.org/10.1002/chem.201403934
State	Published - Sep 11 2014

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/chem.201403934

Cite this

@article{d427a826510b44b0900ed62c56cf33d6,

title = "Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis",

abstract = "An unexpected cationic bis-N-heterocyclic carbene (NHC) benzylidene ether based ruthenium complex (2 a) was prepared through the double incorporation of an unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligand that bore an N-substituted cyclododecyl side chain. The isolation and full characterization (including X-ray diffraction studies) of key synthetic intermediates along with theoretical calculations allowed us to understand the mechanism of the overall cationization process. Finally, the newly developed complex 2 a displayed interesting latent behavior during ring-closing metathesis, which could be {"}switched on{"} under acidic conditions.",

author = "Mathieu Rouen and Pierre Queval and Laura Falivene and Jessica Allard and Toupet, {Lo{\"i}c J.} and Christophe Cr{\'e}visy and Fr{\'e}d{\'e}ric Ca{\"i}jo and Olivier Basl{\'e} and Luigi Cavallo and Marc Mauduit",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: M.M. thanks Rennes Metropole (grant to P.Q.) and the ANR C-Flow-OM (12-CD2I-0002).",

year = "2014",

month = sep,

day = "11",

doi = "10.1002/chem.201403934",

language = "English (US)",

volume = "20",

pages = "13716--13721",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley",

number = "42",

}

TY - JOUR

T1 - Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

AU - Rouen, Mathieu

AU - Queval, Pierre

AU - Falivene, Laura

AU - Allard, Jessica

AU - Toupet, Loïc J.

AU - Crévisy, Christophe

AU - Caïjo, Frédéric

AU - Baslé, Olivier

AU - Cavallo, Luigi

AU - Mauduit, Marc

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: M.M. thanks Rennes Metropole (grant to P.Q.) and the ANR C-Flow-OM (12-CD2I-0002).

PY - 2014/9/11

Y1 - 2014/9/11

N2 - An unexpected cationic bis-N-heterocyclic carbene (NHC) benzylidene ether based ruthenium complex (2 a) was prepared through the double incorporation of an unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligand that bore an N-substituted cyclododecyl side chain. The isolation and full characterization (including X-ray diffraction studies) of key synthetic intermediates along with theoretical calculations allowed us to understand the mechanism of the overall cationization process. Finally, the newly developed complex 2 a displayed interesting latent behavior during ring-closing metathesis, which could be "switched on" under acidic conditions.

AB - An unexpected cationic bis-N-heterocyclic carbene (NHC) benzylidene ether based ruthenium complex (2 a) was prepared through the double incorporation of an unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligand that bore an N-substituted cyclododecyl side chain. The isolation and full characterization (including X-ray diffraction studies) of key synthetic intermediates along with theoretical calculations allowed us to understand the mechanism of the overall cationization process. Finally, the newly developed complex 2 a displayed interesting latent behavior during ring-closing metathesis, which could be "switched on" under acidic conditions.

UR - http://hdl.handle.net/10754/575611

UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201403934

U2 - 10.1002/chem.201403934

DO - 10.1002/chem.201403934

M3 - Article

SN - 0947-6539

VL - 20

SP - 13716

EP - 13721

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 42

ER -

Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 906512: Experimental Crystal Structure Determination : Dichloro-bis(1-cyclododecyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-isopropoxybenzylidene)-ruthenium pentane solvate

CCDC 906511: Experimental Crystal Structure Determination : Chloro-bis(1-cyclododecyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-isopropoxy-4-dimethylaminobenzylidene)-ruthenium tetrafluoroborate chloroform solvate

CCDC 992954: Experimental Crystal Structure Determination : chloro-bis(1-cyclododecyl-3-mesitylimidazol-2-ylidene)-(2-(isopropoxy)benzylidene)-ruthenium tetrafluoroborate ethyl acetate solvate

Cite this

Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 906512: Experimental Crystal Structure Determination : Dichloro-bis(1-cyclododecyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-isopropoxybenzylidene)-ruthenium pentane solvate

CCDC 906511: Experimental Crystal Structure Determination : Chloro-bis(1-cyclododecyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-isopropoxy-4-dimethylaminobenzylidene)-ruthenium tetrafluoroborate chloroform solvate

CCDC 992954: Experimental Crystal Structure Determination : chloro-bis(1-cyclododecyl-3-mesitylimidazol-2-ylidene)-(2-(isopropoxy)benzylidene)-ruthenium tetrafluoroborate ethyl acetate solvate

Cite this