A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes.

Steven Patrick Nolan; Nikolaos Tzouras; Fady Nahra; Laura Falivene; Luigi Cavallo; Marina Saab; Kristof Van Hecke; Alba Collado; Christopher Collett; Andrew Smith; Catherine Cazin

doi:10.1002/chem.202000564

A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes.

Steven Patrick Nolan, Nikolaos Tzouras, Fady Nahra, Laura Falivene, Luigi Cavallo, Marina Saab, Kristof Van Hecke, Alba Collado, Christopher Collett, Andrew Smith, Catherine Cazin

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

15 Scopus citations

Abstract

We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal-N-heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experimental and computational studies provide support for a base-assisted concerted process that does not require free NHC formation. The synthetic protocol was found applicable to a number of Transition Metal- and Main Group-centered NHC compounds and could become the synthetic route of choice to form M-NHC bonds.

Original language	English (US)
Journal	Chemistry (Weinheim an der Bergstrasse, Germany)
DOIs	https://doi.org/10.1002/chem.202000564
State	Published - Feb 6 2020

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10.1002/chem.202000564

https://repository.kaust.edu.sa/bitstream/10754/661483/1/Nolan_et_al-2020-Chemistry_-_A_European_Journal.pdf

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CCDC 1966297: Experimental Crystal Structure Determination : chloro-(2-phenyl-2,5,6,7-tetrahydro-3H-pyrrolo[2,1-c][1,2,4]triazol-3-ylidene)-gold(i)
Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Falivene, L. (Creator), Cavallo, L. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator), Cazin, C. (Creator), Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator) & Cazin, C. (Creator), Cambridge Crystallographic Data Centre, Mar 13 2020
DOI: 10.5517/ccdc.csd.cc2402y6, http://hdl.handle.net/10754/664845
Dataset
CCDC 1966296: Experimental Crystal Structure Determination : 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium bis(chloro)-gold
Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Falivene, L. (Creator), Cavallo, L. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator), Cazin, C. (Creator), Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator) & Cazin, C. (Creator), Cambridge Crystallographic Data Centre, Mar 13 2020
DOI: 10.5517/ccdc.csd.cc2402x5, http://hdl.handle.net/10754/664847
Dataset
CCDC 1966297: Experimental Crystal Structure Determination : chloro-(2-phenyl-2,5,6,7-tetrahydro-3H-pyrrolo[2,1-c][1,2,4]triazol-3-ylidene)-gold(i)
Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Falivene, L. (Creator), Cavallo, L. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator), Cazin, C. (Creator), Nolan, S. P. (Creator), Tzouras, N. (Creator), Nahra, F. (Creator), Saab, M. (Creator), Van Hecke, K. (Creator), Collado, A. (Creator), Collett, C. (Creator), Smith, A. (Creator) & Cazin, C. (Creator), Cambridge Crystallographic Data Centre, Mar 13 2020
DOI: 10.5517/ccdc.csd.cc2402y6, http://hdl.handle.net/10754/664846
Dataset

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@article{1db979e17b704c7c87ba04286cd07aaf,

title = "A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes.",

abstract = "We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal-N-heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experimental and computational studies provide support for a base-assisted concerted process that does not require free NHC formation. The synthetic protocol was found applicable to a number of Transition Metal- and Main Group-centered NHC compounds and could become the synthetic route of choice to form M-NHC bonds.",

author = "Nolan, {Steven Patrick} and Nikolaos Tzouras and Fady Nahra and Laura Falivene and Luigi Cavallo and Marina Saab and {Van Hecke}, Kristof and Alba Collado and Christopher Collett and Andrew Smith and Catherine Cazin",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge VLAIO (SBO project CO2PERATE), King Saud University (Distinguished Scientist Fellowship Program) and King Abdullah University of Science and Technology for support.The Special Research Fund (BOF) of Ghent University is also acknowledged (Doctoral Scholarship to N.V.T.).COST action (CA15106-CHAOS) is thanked for mobility support to N.V.T. Umicore AG is acknowledged for generous gifts of materials.",

year = "2020",

month = feb,

day = "6",

doi = "10.1002/chem.202000564",

language = "English (US)",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley",

}

A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes. / Nolan, Steven Patrick; Tzouras, Nikolaos; Nahra, Fady; Falivene, Laura; Cavallo, Luigi; Saab, Marina; Van Hecke, Kristof; Collado, Alba; Collett, Christopher; Smith, Andrew; Cazin, Catherine.

In: Chemistry (Weinheim an der Bergstrasse, Germany), 06.02.2020.

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

TY - JOUR

T1 - A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes.

AU - Nolan, Steven Patrick

AU - Tzouras, Nikolaos

AU - Nahra, Fady

AU - Falivene, Laura

AU - Cavallo, Luigi

AU - Saab, Marina

AU - Van Hecke, Kristof

AU - Collado, Alba

AU - Collett, Christopher

AU - Smith, Andrew

AU - Cazin, Catherine

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge VLAIO (SBO project CO2PERATE), King Saud University (Distinguished Scientist Fellowship Program) and King Abdullah University of Science and Technology for support.The Special Research Fund (BOF) of Ghent University is also acknowledged (Doctoral Scholarship to N.V.T.).COST action (CA15106-CHAOS) is thanked for mobility support to N.V.T. Umicore AG is acknowledged for generous gifts of materials.

PY - 2020/2/6

Y1 - 2020/2/6

N2 - We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal-N-heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experimental and computational studies provide support for a base-assisted concerted process that does not require free NHC formation. The synthetic protocol was found applicable to a number of Transition Metal- and Main Group-centered NHC compounds and could become the synthetic route of choice to form M-NHC bonds.

AB - We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal-N-heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experimental and computational studies provide support for a base-assisted concerted process that does not require free NHC formation. The synthetic protocol was found applicable to a number of Transition Metal- and Main Group-centered NHC compounds and could become the synthetic route of choice to form M-NHC bonds.

UR - http://hdl.handle.net/10754/661483

UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202000564

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C2 - 32022329

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

ER -

A Mechanistically and Operationally Simple Route to Metal-N-Heterocyclic Carbene (NHC) Complexes.

Abstract

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Other files and links

CCDC 1966297: Experimental Crystal Structure Determination : chloro-(2-phenyl-2,5,6,7-tetrahydro-3H-pyrrolo[2,1-c][1,2,4]triazol-3-ylidene)-gold(i)

CCDC 1966296: Experimental Crystal Structure Determination : 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium bis(chloro)-gold

CCDC 1966297: Experimental Crystal Structure Determination : chloro-(2-phenyl-2,5,6,7-tetrahydro-3H-pyrrolo[2,1-c][1,2,4]triazol-3-ylidene)-gold(i)

Cite this