Efficient alkylation of ketones with primary alcohols catalyzed by ruthenium(II)/P,N ligand complexes |
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| Authors: | Shi-Yuan Liu Lin-Yan Xu Chun-Yu Liu Zhi-Gang Ren David James Young Jian-Ping Lang |
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| Affiliation: | 1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, PR China;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 210032, PR China;3. School of Science, Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor Darul Ehsan, Malaysia;4. Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore, Queensland, 4558, Australia |
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| Abstract: | An efficient catalytic system containing [RuCl2(η6-p-cymene)]2 and one P,N ligand, N-diphenylphosphino-2-aminopyridine (L1) was loaded in catalyzing the alkylation of ketones with primary alcohols for a diverse array of substrates. Other five P,N ligands based on pyridin-2-amine and pyrimidin-2-amine were also examined in this reaction to explore the influence of steric hindrance and electronic effects. Monitoring by 1H NMR and ESI-MS reveals a stable cationic L1-coordinated ruthenium hydride intermediate, identified as [Ru(η6-p-cymene)(κ2-L1)H]+. Organic intermediates consistent with a three-step dehydrogenation, alkylation and hydrogenation pathway were also observed. The final step in this reaction, the ruthenium-catalysed transfer hydrogenation reduction of α,β-unsaturated ketone with benzyl alcohol was performed separately. |
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| Keywords: | P,N hybrid ligand Ruthenium hydride Alkylation Alcohol Ruthenium(II) |
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