Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles

Ho NKT, Reichmann SO, Rottschäfer D, Herbst-Irmer R, Ghadwal R (2017)
Catalysts 7(9): 262.

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Journal Article | Original Article | Published | English
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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.
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Article Processing Charge funded by the Deutsche Forschungsgemeinschaft and the Open Access Publication Fund of Bielefeld University.
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Ho NKT, Reichmann SO, Rottschäfer D, Herbst-Irmer R, Ghadwal R. Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles. Catalysts. 2017;7(9): 262.
Ho, N. K. T., Reichmann, S. O., Rottschäfer, D., Herbst-Irmer, R., & Ghadwal, R. (2017). Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles. Catalysts, 7(9), 262. doi:10.3390/catal7090262
Ho, N. K. T., Reichmann, S. O., Rottschäfer, D., Herbst-Irmer, R., and Ghadwal, R. (2017). Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles. Catalysts 7:262.
Ho, N.K.T., et al., 2017. Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles. Catalysts, 7(9): 262.
N.K.T. Ho, et al., “Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles”, Catalysts, vol. 7, 2017, : 262.
Ho, N.K.T., Reichmann, S.O., Rottschäfer, D., Herbst-Irmer, R., Ghadwal, R.: Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles. Catalysts. 7, : 262 (2017).
Ho, Nga Kim T., Reichmann, Sven O., Rottschäfer, Dennis, Herbst-Irmer, Regine, and Ghadwal, Rajendra. “Expanding the scope of Cu(I) Catalyzed “Click Chemistry” with abnormal NHCs: three-fold click to Tris-Triazoles”. Catalysts 7.9 (2017): 262.
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