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Molecules 2015, 20(4), 7379-7395; doi:10.3390/molecules20047379

Copper(I) Complexes of Mesoionic Carbene: Structural Characterization and Catalytic Hydrosilylation Reactions

Institut für Chemie und Biochemie, Anorganische Chemie, Freie Universität Berlin, Fabeckstraße 34-36, Berlin D-14195, Germany
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Author to whom correspondence should be addressed.
Academic Editor: Arnaud Gautier
Received: 24 February 2015 / Revised: 20 March 2015 / Accepted: 23 March 2015 / Published: 22 April 2015
(This article belongs to the Special Issue Advances in Click Chemistry)
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Abstract

Two series of different Cu(I)-complexes of “click” derived mesoionic carbenes are reported. Halide complexes of the type (MIC)CuI (with MIC = 1,4-(2,6-diisopropyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (for 1b), 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 1c)) and cationic complexes of the general formula [Cu(MIC)2]X (with MIC =1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene, X = CuI2 (for ), 1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene, X = BF4 (for 2a), 1,4-(2,6-diisopropyl)phenyl-3-methyl-1,2,3-triazol-5-ylidene, X = BF4 (for 2b), 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene, X = BF4 (for 2c)) have been prepared from CuI or [Cu(CH3CN)4](BF4) and the corresponding ligands, respectively. All complexes were characterized by elemental analysis and standard spectroscopic methods. Complexes 2á and 1b were studied by single-crystal X-ray diffraction analysis. Structural analysis revealed 2á to adopt a cationic form as [Cu(MIC)2](CuI2) and comparison of the NMR spectra of 2á and 2a confirmed this conformation in solution. In contrast, after crystallization complex 1b was found to adopt the desired neutral form. All complexes were tested for the reduction of cyclohexanone under hydrosilylation condition at elevated temperatures. These complexes were found to be efficient catalysts for this reaction. 2c was also found to catalyze this reaction at room temperature. Mechanistic studies have been carried out as well. View Full-Text
Keywords: click chemistry; mesoionic carbenes; triazolylidenes; copper complexes; hydrosilylation; catalysis click chemistry; mesoionic carbenes; triazolylidenes; copper complexes; hydrosilylation; catalysis
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MDPI and ACS Style

Hohloch, S.; Duecker, F.L.; van der Meer, M.; Sarkar, B. Copper(I) Complexes of Mesoionic Carbene: Structural Characterization and Catalytic Hydrosilylation Reactions. Molecules 2015, 20, 7379-7395.

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