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Catalysts 2017, 7(9), 262; doi:10.3390/catal7090262

Expanding the Scope of Cu(I) Catalyzed “Click Chemistry” with Abnormal NHCs: Three-Fold Click to Tris-Triazoles

1
Anorganische Molekülchemie und Katalyse, Lehrstuhl für Anorganische Chemie und Strukturchemie, Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, D-33615 Bielefeld, Germany
2
Centrum für Molekulare Materialien, Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, D-33615 Bielefeld, Germany
3
Institut für Anorganische Chemie der Georg-August-Universität Göttingen, Tammannstraße 4, D-37077 Göttingen, Germany
*
Author to whom correspondence should be addressed.
Received: 10 August 2017 / Revised: 25 August 2017 / Accepted: 28 August 2017 / Published: 1 September 2017
(This article belongs to the Special Issue Tailor-Made NHC Ligands)
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Abstract

Cationic copper(I) complexes [Cu(aIPrPh)(IPr)]I (3) and [Cu(aIPrPh)2]I (4) featuring an abnormal N-heterocyclic carbene (aNHC) (aIPrPh = 1,3-bis(2,6-diisopropylphenyl)-2-phenyl- imidazol-4-ylidene) and/or an NHC (IPr = 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene) ligand(s) are reported. Treatment of Cu(aIPrPh)I (2) with IPr affords complex 3. Reaction of (IPrPh)I (1) (IPrPh = 1,3-bis(2,6-diisopropylphenyl)-2-phenyl-imidazolium) with CuI in the presence of K{N(SiMe3)2} leads to the formation of 4. Complexes 3 and 4 represent rare examples of mixed aNHC-NHC and bis-aNHC metal complexes, respectively. They are characterized by elemental analysis, NMR spectroscopic, and mass spectrometric studies. The solid-state molecular structures of 3 and 4 have been determined by single crystal X-ray diffraction analyses. The catalytic activity of 2, 3, and 4 has been investigated in the [3+2] cycloaddition of alkynes and organic azides, affording triazole derivatives in an almost quantitative yield. Notably, complexes 2, 3, and 4 are excellent catalysts for the three-fold cycloaddition of a tris-azide with various alkynes. This catalytic protocol offers a high yield access to tris-triazoles in a shorter reaction time and considerably reduces the experimental work-up compared to the classical synthetic method. View Full-Text
Keywords: abnormal carbene; click reaction; copper; [3+2] cycloaddition; N-heterocyclic carbene; tris-triazoles; structure; catalysis abnormal carbene; click reaction; copper; [3+2] cycloaddition; N-heterocyclic carbene; tris-triazoles; structure; catalysis
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MDPI and ACS Style

Ho, N.K.T.; Reichmann, S.O.; Rottschäfer, D.; Herbst-Irmer, R.; Ghadwal, R.S. Expanding the Scope of Cu(I) Catalyzed “Click Chemistry” with Abnormal NHCs: Three-Fold Click to Tris-Triazoles. Catalysts 2017, 7, 262.

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