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

dc.contributor.authorHo, Nga Kim T.
dc.contributor.authorReichmann, Sven O.
dc.contributor.authorRottschäfer, Dennis
dc.contributor.authorHerbst-Irmer, Regine
dc.contributor.authorGhadwal, Rajendra S.
dc.date.accessioned2019-12-17T13:03:29Z
dc.date.available2019-12-17T13:03:29Z
dc.date.issued2017de
dc.relation.ISSN2073-4344de
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?gs-1/17014
dc.description.abstractCationic 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-phenylimidazol- 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.de
dc.language.isoengde
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectabnormal carbene; click reaction; copper; [3+2] cycloaddition; N-heterocyclic carbene; tris-triazoles; structure; catalysisde
dc.subject.ddc540
dc.titleExpanding the Scope of Cu(I) Catalyzed “Click Chemistry” with Abnormal NHCs: Three-Fold Click to Tris-Triazolesde
dc.typejournalArticlede
dc.identifier.doi10.3390/catal7090262
dc.type.versionpublishedVersionde
dc.relation.eISSN2073-4344
dc.bibliographicCitation.volume7de
dc.bibliographicCitation.issue9de
dc.bibliographicCitation.firstPage262de
dc.type.subtypejournalArticle
dc.description.statuspeerReviewedde
dc.bibliographicCitation.journalCatalystsde


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