期刊
CHEMCATCHEM
卷 14, 期 7, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202200086
关键词
aqueous hydrogenation; carbohydrates; iridium; ligand effects; N-heterocyclic carbene
资金
- Marie Sklodowska-Curie Individual Fellowship [749549]
- European Research Council [CoG 615653]
- Royal Society of Chemistry Researcher Mobility Grant
- Swiss National Science Foundation [206021_128724]
- Universitat Bern
- UK EPSCRS [EP/L015633/1]
- Marie Curie Actions (MSCA) [749549] Funding Source: Marie Curie Actions (MSCA)
Two sets of carbohydrate-NHC hybrid iridium complexes were synthesized to combine properties of carbohydrates and triazolylidene ligands in organometallic catalysis. The complexes efficiently catalyzed the direct hydrogenation of ketones in water, with the catalytic activity influenced by the pH of the aqueous medium. The directly linked systems induced a moderate enantiomeric excess.
Two sets of carbohydrate-NHC hybrid iridium complexes were synthesised in order to combine properties of carbohydrates and triazolylidene (trz) ligands in organometallic catalysis. One set features a direct trz linkage to the anomeric carbohydrate carbon, while the second set is comprised of an ethyl linker between the two functional units. Deprotection of the carbohydrate afforded hybrid complexes that efficiently catalyse the direct hydrogenation of ketones in water. The catalytic activity of the hybrid complexes was influenced by the pH of the aqueous medium and surpassed the activity of carbohydratefree or acetyl-protected analogues (>90% vs 13% yield). While no enantiomeric induction was observed for the ethyl-linked hybrids, a moderate enantiomeric excess (ee) was induced by the directly linked systems. Moreover, these carbohydrate-trz hybrid complexes displayed mixed inhibitory activity towards a glycosidase from H. orenii that contain a glucose binding site.
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