Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts

Yannick D. Bidal; César A. Urbina-Blanco; Albert Poater; David B. Cordes; Alexandra M. Z. Slawin; Luigi Cavallo; Catherine S. J. Cazin

doi:10.1039/c9dt01811e

Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts

Yannick D. Bidal, César A. Urbina-Blanco, Albert Poater, David B. Cordes, Alexandra M. Z. Slawin, Luigi Cavallo, Catherine S. J. Cazin

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

8 Scopus citations

Abstract

Five new complexes [RuCl2(SIMes)(Ind)(O-pXC5H4)] bearing different para-substituted triphenylphosphites (X = H, OCH3, CF3, Cl, SF5 and CN) were synthesised and used to study the effect of the electronic properties of the phosphite on olefin metathesis activity. Investigations of the physical properties of the new ligands and complexes were performed using physicochemical and DFT calculations. The catalytic activity of the complexes was benchmarked in challenging ring closing metathesis transformations featuring the formation of tetra-substituted double bonds. Complex [RuCl2(SIMes)(Ind)P(O-pCF3C5H4)3] (3c) exhibited a particularly high catalytic activity, superior to state-of-the-art catalysts, and was further tested on a wide range of substrates.

Original language	English (US)
Pages (from-to)	11326-11337
Number of pages	12
Journal	Dalton Transactions
Volume	48
Issue number	30
DOIs	https://doi.org/10.1039/c9dt01811e
State	Published - 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC), the EC (CP-FP 211468-2 EUMET and CIG09-GA-2011-293900) and the MICINN (PGC2018-097722-B-I00 to AP) for funding.

Access to Document

10.1039/c9dt01811e

https://repository.kaust.edu.sa/bitstream/10754/656059/1/YB_Dalton_MS_Revision.pdf

Cite this

@article{04de81ba65c14db694d4f98917c94fad,

title = "Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts",

abstract = "Five new complexes [RuCl2(SIMes)(Ind)(O-pXC5H4)] bearing different para-substituted triphenylphosphites (X = H, OCH3, CF3, Cl, SF5 and CN) were synthesised and used to study the effect of the electronic properties of the phosphite on olefin metathesis activity. Investigations of the physical properties of the new ligands and complexes were performed using physicochemical and DFT calculations. The catalytic activity of the complexes was benchmarked in challenging ring closing metathesis transformations featuring the formation of tetra-substituted double bonds. Complex [RuCl2(SIMes)(Ind)P(O-pCF3C5H4)3] (3c) exhibited a particularly high catalytic activity, superior to state-of-the-art catalysts, and was further tested on a wide range of substrates.",

author = "Bidal, {Yannick D.} and Urbina-Blanco, {C{\'e}sar A.} and Albert Poater and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Luigi Cavallo and Cazin, {Catherine S. J.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC), the EC (CP-FP 211468-2 EUMET and CIG09-GA-2011-293900) and the MICINN (PGC2018-097722-B-I00 to AP) for funding.",

year = "2019",

doi = "10.1039/c9dt01811e",

language = "English (US)",

volume = "48",

pages = "11326--11337",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "30",

}

TY - JOUR

T1 - Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts

AU - Bidal, Yannick D.

AU - Urbina-Blanco, César A.

AU - Poater, Albert

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Cavallo, Luigi

AU - Cazin, Catherine S. J.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC), the EC (CP-FP 211468-2 EUMET and CIG09-GA-2011-293900) and the MICINN (PGC2018-097722-B-I00 to AP) for funding.

PY - 2019

Y1 - 2019

N2 - Five new complexes [RuCl2(SIMes)(Ind)(O-pXC5H4)] bearing different para-substituted triphenylphosphites (X = H, OCH3, CF3, Cl, SF5 and CN) were synthesised and used to study the effect of the electronic properties of the phosphite on olefin metathesis activity. Investigations of the physical properties of the new ligands and complexes were performed using physicochemical and DFT calculations. The catalytic activity of the complexes was benchmarked in challenging ring closing metathesis transformations featuring the formation of tetra-substituted double bonds. Complex [RuCl2(SIMes)(Ind)P(O-pCF3C5H4)3] (3c) exhibited a particularly high catalytic activity, superior to state-of-the-art catalysts, and was further tested on a wide range of substrates.

AB - Five new complexes [RuCl2(SIMes)(Ind)(O-pXC5H4)] bearing different para-substituted triphenylphosphites (X = H, OCH3, CF3, Cl, SF5 and CN) were synthesised and used to study the effect of the electronic properties of the phosphite on olefin metathesis activity. Investigations of the physical properties of the new ligands and complexes were performed using physicochemical and DFT calculations. The catalytic activity of the complexes was benchmarked in challenging ring closing metathesis transformations featuring the formation of tetra-substituted double bonds. Complex [RuCl2(SIMes)(Ind)P(O-pCF3C5H4)3] (3c) exhibited a particularly high catalytic activity, superior to state-of-the-art catalysts, and was further tested on a wide range of substrates.

UR - http://hdl.handle.net/10754/656059

UR - http://xlink.rsc.org/?DOI=C9DT01811E

UR - http://www.scopus.com/inward/record.url?scp=85070095804&partnerID=8YFLogxK

U2 - 10.1039/c9dt01811e

DO - 10.1039/c9dt01811e

M3 - Article

C2 - 31273362

SN - 1477-9226

VL - 48

SP - 11326

EP - 11337

JO - Dalton Transactions

JF - Dalton Transactions

IS - 30

ER -

Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

CCDC 1023425: Experimental Crystal Structure Determination : dichloro-[1-isopropyl-4-methylbenzene]-{tris[4-(trifluoromethyl)phenyl] phosphite}-ruthenium

CCDC 1023432: Experimental Crystal Structure Determination : [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro-(3-phenyl-1H-inden-1-ylidene)-{tris[4-(pentafluoro-lambda6-sulfanyl)phenyl] phosphite}-ruthenium unknown solvate

CCDC 1023430: Experimental Crystal Structure Determination : [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro-(3-phenyl-1H-inden-1-ylidene)-{tris[4-(trifluoromethyl)phenyl] phosphite}-ruthenium unknown solvate

Cite this

Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1023425: Experimental Crystal Structure Determination : dichloro-[1-isopropyl-4-methylbenzene]-{tris[4-(trifluoromethyl)phenyl] phosphite}-ruthenium

CCDC 1023432: Experimental Crystal Structure Determination : [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro-(3-phenyl-1H-inden-1-ylidene)-{tris[4-(pentafluoro-lambda6-sulfanyl)phenyl] phosphite}-ruthenium unknown solvate

CCDC 1023430: Experimental Crystal Structure Determination : [1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro-(3-phenyl-1H-inden-1-ylidene)-{tris[4-(trifluoromethyl)phenyl] phosphite}-ruthenium unknown solvate

Cite this