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  Continuous-Flow Asymmetric Hydrogenation of an Enol Ester by using Supercritical Carbon Dioxide: Ionic Liquids versus Supported Ionic Liquids as the Catalyst Matrix

Zhang, Z., Franciò, G., & Leitner, W. (2015). Continuous-Flow Asymmetric Hydrogenation of an Enol Ester by using Supercritical Carbon Dioxide: Ionic Liquids versus Supported Ionic Liquids as the Catalyst Matrix. ChemCatChem, 7(13), 1961-1965. doi:10.1002/cctc.201500295.

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 Creators:
Zhang, Ziyun1, Author
Franciò, Giancarlo 1, Author
Leitner, Walter2, Author           
Affiliations:
1Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen (Germany), ou_persistent22              
2Research Group Leitner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445610              

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Free keywords: asymmetric catalysis; hydrogenation; ionic liquids; phosphane ligands; rhodium
 Abstract: The continuous-flow Rh-catalyzed asymmetric hydrogenation of the enol ester 1-(trifluoromethyl)vinyl acetate was investigated by using supercritical carbon dioxide (scCO2) as the mobile phase and either ionic liquids (IL) or supported ionic liquids (SILP) as the catalyst matrix. Three molecular catalysts based on chiral ligands were evaluated. The catalyst based on the phosphine-phosphoramidite ligand (Sa,Rc)-Xyl-QUINAPHOS in combination with the SILP/scCO2 immobilization strategy provided the most effective system under continuous-flow conditions and gave a remarkably stable performance. During 233 h on stream, high single-pass conversions (90–70 %), slightly increased enantioselectivity (80–84 % ee), and a turnover number of 70 400 were observed; this turnover number shows a six-fold increase over that achieved in the IL/scCO2 system with the same catalyst.

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Language(s): eng - English
 Dates: 2015-07-022015-07-03
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/cctc.201500295
 Degree: -

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Title: ChemCatChem
  Other : ChemCatChem
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 7 (13) Sequence Number: - Start / End Page: 1961 - 1965 Identifier: ISSN: 1867-3880
CoNE: https://pure.mpg.de/cone/journals/resource/1867-3880