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

61 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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@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 (Weinheim an der Bergstrasse, Germany)",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

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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

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DO - 10.1002/chem.202000564

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JO - Chemistry (Weinheim an der Bergstrasse, Germany)

JF - Chemistry (Weinheim an der Bergstrasse, Germany)

ER -

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

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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)

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)

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

Abstract

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Datasets

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)

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