Transition Metal Complexes of an (S,S)-1,2-Diphenylethylamine-Functionalized N-Heterocyclic Carbene: A New Member of the Asymmetric NHC Ligand Family
| Autor: | Kai Y. Wan, Robert H. Morris, Alan J. Lough |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Trimethylsilyl
010405 organic chemistry Ligand Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences 0104 chemical sciences 3. Good health Ruthenium Inorganic Chemistry chemistry.chemical_compound Enantiopure drug chemistry Amide Polymer chemistry Organic chemistry Iridium Physical and Theoretical Chemistry Carbene Acetophenone |
| Zdroj: | Organometallics. 35:1604-1612 |
| ISSN: | 1520-6041 0276-7333 |
| Popis: | By a simple SN2 reaction between N-methylimidazole and a chiral sulfamidate, the first proligand of a new class of enantiopure NHC-CHPh-CHPh-NH2 ligands can be prepared in high yield. This proligand, with the molecular formula [(S,S)-H2NCHPhCHPh-NC3H3N-CH3](PF6), when reacted with a slight excess of lithium or potassium bis(trimethylsilyl)amide, produces the corresponding NHC-CHPh-CHPh-NH2 ligand, “kaibene”. In the presence of the silver(I) starting material AgPF6 or AgI, two Ag(kaibene)2X complexes (X = PF6 or I) and one helical kaibene silver polymer, [Ag(kaibene)]n(PF6)n, can be prepared. Using the suitable silver complex, we successfully transferred kaibene to ruthenium(II), iridium(I), and nickel(II). The ruthenium complex [Ru(p-cymene)(kaibene)(Cl)]PF6 with a base in THF is a moderately active catalyst at 50 °C and 25 bar of H2 for the hydrogenation of acetophenone but with no enantioselectivity. |
| Databáze: | OpenAIRE |
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