Multicomponent Synthesis of N-Heterocyclic Carbene Complexes

R.S. Bon; F.J.J. de Kanter; M. Lutz; A.L Spek; M.C. Jahnke; F.E. Hahn; M.B. Groen; R.V.A. Orru

doi:10.1021/om070168u

Multicomponent Synthesis of N-Heterocyclic Carbene Complexes

R.S. Bon, F.J.J. de Kanter, M. Lutz, A.L Spek, M.C. Jahnke, F.E. Hahn, M.B. Groen, R.V.A. Orru

Organic Chemistry

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

N-Heterocyclic carbenes (NHCs) are valuable ligands in transition metal catalysis, due to their unique electronic properties. However, only a few routes toward unsymmetrically substituted, saturated NHCs are known. We have successfully applied the multicomponent synthesis of 2H-2-imidazolines for the preparation of a range of diversely substituted imidazolidin-2-ylidene complexes under mild conditions. In the desired NHC precursors the substituents at N-1, N-3, C-4, and C-5 were varied easily and independently by choosing the appropriate amine, aldehyde, isocyanide, or halide as starting material. Subsequent formation of the imidazolium salts followed by deprotonation with KO

Original language	English
Pages (from-to)	3639-3650
Journal	Organometallics
Volume	26
DOIs	https://doi.org/10.1021/om070168u
Publication status	Published - 2007

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10.1021/om070168u

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CCDC 612942: Experimental Crystal Structure Determination
Bon, R. S. (Contributor), De Kanter, F. J. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Jahnke, M. C. (Contributor), Hahn, F. E. (Contributor), Groen, M. B. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 1 Jan 2007
DOI: 10.5517/ccnktbb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnktbb&sid=DataCite
Dataset / Software: Dataset
CCDC 612938: Experimental Crystal Structure Determination
Bon, R. S. (Contributor), De Kanter, F. J. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Jahnke, M. C. (Contributor), Hahn, F. E. (Contributor), Groen, M. B. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 1 Jan 2007
DOI: 10.5517/ccnkt66, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnkt66&sid=DataCite
Dataset / Software: Dataset
CCDC 612939: Experimental Crystal Structure Determination
Bon, R. S. (Contributor), De Kanter, F. J. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Jahnke, M. C. (Contributor), Hahn, F. E. (Contributor), Groen, M. B. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 1 Jan 2007
DOI: 10.5517/ccnkt77, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnkt77&sid=DataCite
Dataset / Software: Dataset

Cite this

@article{583d85794f48482199e8f2425ff92504,

title = "Multicomponent Synthesis of N-Heterocyclic Carbene Complexes",

abstract = "N-Heterocyclic carbenes (NHCs) are valuable ligands in transition metal catalysis, due to their unique electronic properties. However, only a few routes toward unsymmetrically substituted, saturated NHCs are known. We have successfully applied the multicomponent synthesis of 2H-2-imidazolines for the preparation of a range of diversely substituted imidazolidin-2-ylidene complexes under mild conditions. In the desired NHC precursors the substituents at N-1, N-3, C-4, and C-5 were varied easily and independently by choosing the appropriate amine, aldehyde, isocyanide, or halide as starting material. Subsequent formation of the imidazolium salts followed by deprotonation with KO",

author = "R.S. Bon and {de Kanter}, F.J.J. and M. Lutz and A.L Spek and M.C. Jahnke and F.E. Hahn and M.B. Groen and R.V.A. Orru",

year = "2007",

doi = "10.1021/om070168u",

language = "English",

volume = "26",

pages = "3639--3650",

journal = "Organometallics",

issn = "1520-6041",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Multicomponent Synthesis of N-Heterocyclic Carbene Complexes

AU - Bon, R.S.

AU - de Kanter, F.J.J.

AU - Lutz, M.

AU - Spek, A.L

AU - Jahnke, M.C.

AU - Hahn, F.E.

AU - Groen, M.B.

AU - Orru, R.V.A.

PY - 2007

Y1 - 2007

N2 - N-Heterocyclic carbenes (NHCs) are valuable ligands in transition metal catalysis, due to their unique electronic properties. However, only a few routes toward unsymmetrically substituted, saturated NHCs are known. We have successfully applied the multicomponent synthesis of 2H-2-imidazolines for the preparation of a range of diversely substituted imidazolidin-2-ylidene complexes under mild conditions. In the desired NHC precursors the substituents at N-1, N-3, C-4, and C-5 were varied easily and independently by choosing the appropriate amine, aldehyde, isocyanide, or halide as starting material. Subsequent formation of the imidazolium salts followed by deprotonation with KO

AB - N-Heterocyclic carbenes (NHCs) are valuable ligands in transition metal catalysis, due to their unique electronic properties. However, only a few routes toward unsymmetrically substituted, saturated NHCs are known. We have successfully applied the multicomponent synthesis of 2H-2-imidazolines for the preparation of a range of diversely substituted imidazolidin-2-ylidene complexes under mild conditions. In the desired NHC precursors the substituents at N-1, N-3, C-4, and C-5 were varied easily and independently by choosing the appropriate amine, aldehyde, isocyanide, or halide as starting material. Subsequent formation of the imidazolium salts followed by deprotonation with KO

U2 - 10.1021/om070168u

DO - 10.1021/om070168u

M3 - Article

SN - 1520-6041

VL - 26

SP - 3639

EP - 3650

JO - Organometallics

JF - Organometallics

ER -

Multicomponent Synthesis of N-Heterocyclic Carbene Complexes

Abstract

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Datasets

CCDC 612942: Experimental Crystal Structure Determination

CCDC 612938: Experimental Crystal Structure Determination

CCDC 612939: Experimental Crystal Structure Determination

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