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

Research output: Contribution to JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)3639-3650
JournalOrganometallics
Volume26
DOIs
Publication statusPublished - 2007

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carbenes
synthesis
Deprotonation
Cyanides
aldehydes
Aldehydes
Electronic properties
Catalysis
catalysis
halides
Amines
Transition metals
amines
Salts
transition metals
routes
Ligands
salts
preparation
ligands

Cite this

Bon, R. S., de Kanter, F. J. J., Lutz, M., Spek, A. L., Jahnke, M. C., Hahn, F. E., ... Orru, R. V. A. (2007). Multicomponent Synthesis of N-Heterocyclic Carbene Complexes. Organometallics, 26, 3639-3650. https://doi.org/10.1021/om070168u
Bon, R.S. ; de Kanter, F.J.J. ; Lutz, M. ; Spek, A.L ; Jahnke, M.C. ; Hahn, F.E. ; Groen, M.B. ; Orru, R.V.A. / Multicomponent Synthesis of N-Heterocyclic Carbene Complexes. In: Organometallics. 2007 ; Vol. 26. pp. 3639-3650.
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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",
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Bon, RS, de Kanter, FJJ, Lutz, M, Spek, AL, Jahnke, MC, Hahn, FE, Groen, MB & Orru, RVA 2007, 'Multicomponent Synthesis of N-Heterocyclic Carbene Complexes' Organometallics, vol. 26, pp. 3639-3650. https://doi.org/10.1021/om070168u

Multicomponent Synthesis of N-Heterocyclic Carbene Complexes. / Bon, R.S.; de Kanter, F.J.J.; Lutz, M.; Spek, A.L; Jahnke, M.C.; Hahn, F.E.; Groen, M.B.; Orru, R.V.A.

In: Organometallics, Vol. 26, 2007, p. 3639-3650.

Research output: Contribution to JournalArticleAcademicpeer-review

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

VL - 26

SP - 3639

EP - 3650

JO - Organometallics

JF - Organometallics

SN - 1520-6041

ER -

Bon RS, de Kanter FJJ, Lutz M, Spek AL, Jahnke MC, Hahn FE et al. Multicomponent Synthesis of N-Heterocyclic Carbene Complexes. Organometallics. 2007;26:3639-3650. https://doi.org/10.1021/om070168u