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

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
Pages (from-to)	11326-11337
Number of pages	12
Journal	Dalton Transactions
Volume	48
Issue number	30
Early online date	5 Jul 2019
DOIs	https://doi.org/10.1039/C9DT01811E
Publication status	Published - 14 Aug 2019

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10.1039/C9DT01811E

Bidal_2019_DT_Electroniceffects_AAM
Copyright © 2019 The Author(s). This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C9DT01811E
Accepted author manuscript, 907 KB

EUMET: EU FP7 'EUMET' Olefin Metathesis as a Practical Synthetic Tool
Nolan, S. P. (PI)
European Commission
1/11/08 → 31/10/12
Project: Standard

Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts (dataset)
Bidal, Y. D. (Creator), Urbina Blanco, C. A. (Creator), Poater, A. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Cavallo, L. (Creator) & Cazin, C. S. J. (Creator), Cambridge Crystallographic Data Centre, 2019
https://dx.doi.org/10.5517/ccdc.csd.cc13byp2 and 9 more links, https://dx.doi.org/10.5517/ccdc.csd.cc13byq3, https://dx.doi.org/10.5517/ccdc.csd.cc13byr4, https://dx.doi.org/10.5517/ccdc.csd.cc13bys5, https://dx.doi.org/10.5517/ccdc.csd.cc13byt6, https://dx.doi.org/10.5517/ccdc.csd.cc13byv7, https://dx.doi.org/10.5517/ccdc.csd.cc13byw8, https://dx.doi.org/10.5517/ccdc.csd.cc13byx9, https://dx.doi.org/10.5517/ccdc.csd.cc13byyb, https://dx.doi.org/10.5517/ccdc.csd.cc13byzc (show fewer)
Dataset

Cite this

@article{d6434eff9aa44f9d8cd560c98109a339,

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 = "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",

month = aug,

day = "14",

doi = "10.1039/C9DT01811E",

language = "English",

volume = "48",

pages = "11326--11337",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "ROYAL SOC 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 - 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 - 2019/8/14

Y1 - 2019/8/14

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.

U2 - 10.1039/C9DT01811E

DO - 10.1039/C9DT01811E

M3 - Article

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

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Projects

EUMET: EU FP7 'EUMET' Olefin Metathesis as a Practical Synthetic Tool

Datasets

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

Cite this