Formation of chiral ionic liquids and imidazol-2-ylidene metal complexes from the proteinogenic aminoacid l-histidine |
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| Affiliation: | 1. Institute of Biophysical Chemistry, Center for Biomolecular Magnetic Resonance, and Frankfurt Institute for Advanced Studies, Goethe University Frankfurt am Main, Max-von-Laue-Str. 9, 60438 Frankfurt am Main, Germany;2. Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan;3. Structural Biology Research Center, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan;1. State Key Laboratory of High Performance Ceramics and Superfine Microstructure, Shanghai Institute of Ceramics, Chinese Academy of Sciences, Shanghai 200050, China;2. Graduate University of Chinese Academy of Sciences, Beijing 100049, China;1. National University Health System, 1E Kent Ridge Road, Singapore 119228, Singapore;2. National University of Singapore, Level 9 6 Science Drive 2, Singapore 117546, Singapore |
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| Abstract: | ![]()
Treatment of the amino acid derivative Bz-His-OMe with excess n-propyl bromide gave the corresponding histidinium salt [Bz-His(n-propyl)2-OMe+Br−]. It features a melting point of 39 °C and may serve as a useful readily available optically active ionic liquid. Its subsequent treatment with silver oxide gave the corresponding l-histidine derived chiral N-heterocyclic carbene complex [“(carbene)2Ag · AgBr2”]. Transmetallation by treatment with Pd(CH3CN)2Cl2 or [Rh(cod)Cl]2 led to the formation of the respective chiral late metal imidazol-2-ylidene complexes [“(carbene)2PdCl2”] and [“(carbene)RhCl(cod)”], respectively. Four diastereomers of the square planar palladium system were observed. Due to the additional chirality center in the l-histidine-derived “Arduengo-carbene ligand” two diastereomers of the rhodium carbene complex were formed. |
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