Ruthenium/1,1′-Bis(diphenylphosphino)ferrocene-Catalysed Oppenauer Oxidation of Alcohols and Lactonisation of α,ω-Diols using Methyl Isobutyl Ketone as Oxidant
| Autor: | Celine M. Nicklaus, Pim Huat Phua, Hero J. Heeres, Sébastien Noël, Teddy Buntara, Johannes G. de Vries |
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| Přispěvatelé: | Stratingh Institute of Chemistry, Synthetic Organic Chemistry, Chemical Technology, UCCS Équipe Catalyse Supramoléculaire, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille-Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille |
| Rok vydání: | 2013 |
| Předmět: |
inorganic chemicals
ketones oxidation DIOLS Oppenauer oxidation chemistry.chemical_element HIGH CATALYTIC-ACTIVITIES 010402 general chemistry 01 natural sciences alcohols Catalysis chemistry.chemical_compound HYDROGEN-PEROXIDE aldehydes 1 1'-Bis(diphenylphosphino)ferrocene [CHIM]Chemical Sciences Organic chemistry heterocyclic compounds ligand effects GeneralLiterature_REFERENCE(e.g. dictionaries encyclopedias glossaries) ComputingMilieux_MISCELLANEOUS 010405 organic chemistry LACTONES SECONDARY ALCOHOLS DEHYDROGENATIVE CYCLIZATION CETYLPYRIDINIUM CHLORIDE General Chemistry SELECTIVE OXIDATION homogeneous catalysis 0104 chemical sciences 3. Good health Ruthenium 2-PHASE CONDITIONS Methyl isobutyl ketone HETEROCYCLIC CARBENE COMPLEXES chemistry Ferrocene Alcohol oxidation Caprolactone |
| Zdroj: | Advanced Synthesis & Catalysis, 355(14-15), 2839-2844. WILEY-V C H VERLAG GMBH Advanced Synthesis and Catalysis Advanced Synthesis and Catalysis, 2013, 355 (14-15), pp.2839-2844. ⟨10.1002/adsc.201300438⟩ Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2013, 355 (14-15), pp.2839-2844. ⟨10.1002/adsc.201300438⟩ |
| ISSN: | 1615-4150 1615-4169 |
| DOI: | 10.1002/adsc.201300438 |
| Popis: | A number of ruthenium catalysts, made in situ from [Ru(p-cymene)Cl-2](2) and various monodentate and bidentate phosphorus ligands were screened in the double Oppenauer oxidation of 1,6-hexanediol to caprolactone using methyl isobutyl ketone as oxidant and potassium carbonate as base. The catalyst based on 1,1-bis(diphenylphosphinyl)ferrocene gave this lactone in excellent yield. The same catalyst was evaluated for the oxidation of other diols to their lactones, of primary alcohols to the corresponding aldehydes and of secondary alcohols to the ketones under the same reaction conditions. The products were obtained in moderate to excellent yields. |
| Databáze: | OpenAIRE |
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