Asymmetric Transfer Hydrogenation in Water with a Supported Noyori−Ikariya Catalyst

Xiaoguang Li,† Xiaofeng Wu,† Weiping Chen,† Fred E. Hancock,‡ Frank King,‡ and Jianliang Xiao*†
Department of Chemistry, Liverpool Center for Materials and Catalysis, University of Liverpool, Liverpool L69 7ZD, UK, and Johnson Matthey, Billingham, Cleveland TS23 1LB, UK
Org. Lett., 2004, 6 (19), pp 3321–3324
DOI: 10.1021/ol0487175
Publication Date (Web): August 20, 2004
Copyright © 2004 American Chemical Society
Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Abstract Image

The poly(ethylene glycol)-supported ruthenium precatalyst shown above is highly effective for asymmetric transfer hydrogenation of unfunctionalized aromatic ketones by HCOONa in neat water, affording fast rates, good to excellent enantioselectivities, and outstanding reusability.

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This article has been cited by 19 ACS Journal articles (5 most recent appear below).

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    Transfer Hydrogenation in Water via a Ruthenium Catalyst with OH Groups near the Metal Center on a bipy Scaffold

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    • Transfer Hydrogenation in Water via a Ruthenium Catalyst with OH Groups near the Metal Center on a bipy Scaffold

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      The new ligand 6,6′-dihydroxy-2,2′-bipyridyl (dhbp) was synthesized via its tautomer, and this provides an efficient route to novel metal complexes of dhbp. In ruthenium complexes of dhbp, these OH groups enhance water solubility and may play a role in ...

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  • Cover Image

    Single-Chain Folding of Polymers for Catalytic Systems in Water

    Takaya Terashima, Tristan Mes, Tom F. A. De Greef, Martijn A. J. Gillissen, Pol Besenius, Anja R. A. Palmans, and E. W. Meijer
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    • Single-Chain Folding of Polymers for Catalytic Systems in Water

      Takaya Terashima, Tristan Mes, Tom F. A. De Greef, Martijn A. J. Gillissen, Pol Besenius, Anja R. A. Palmans, and E. W. Meijer
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      Enzymes are a source of inspiration for chemists attempting to create versatile synthetic catalysts. In order to arrive at a polymeric chain carrying catalytic units separated spatially, it is a prerequisite to fold these polymers in water into well-...

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  • Cover Image

    Support and Size Effects of Ruthenium Catalysts with a Chiral Modifier for Asymmetric Hydrogenation of Aromatic Ketones

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    The Journal of Physical Chemistry C2010 114 (46), 19752-19760

    • Support and Size Effects of Ruthenium Catalysts with a Chiral Modifier for Asymmetric Hydrogenation of Aromatic Ketones

      Linmin Ye, Haiqiang Lin, Hancheng Zhou, and Youzhu Yuan
      The Journal of Physical Chemistry C2010 114 (46), 19752-19760

      A series of supported Ru catalysts with achiral modifier triphenylphosphine (TPP) and chiral modifier (1R,2R)-1,2-diphenylethylenediamine [(1R,2R)-DPEN] were employed for the asymmetric hydrogenation of aromatic ketones. The textural and structural ...

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  • Cover Image

    Water: Nature’s Reaction Enforcer—Comparative Effects for Organic Synthesis “In-Water” and “On-Water”

    Richard N. Butler and Anthony G. Coyne
    Chemical Reviews2010 110 (10), 6302-6337

    • Water: Nature’s Reaction Enforcer—Comparative Effects for Organic Synthesis “In-Water” and “On-Water”

      Richard N. Butler and Anthony G. Coyne
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      Abstract | HTMLFull Text HTML | PDFHi-Res PDF | PDFPDF w/ Links
  • Cover Image

    New Dipyridylamine Ruthenium Complexes for Transfer Hydrogenation of Aryl Ketones in Water

    Charles Romain, Sylvain Gaillard, Mohammed K. Elmkaddem, Loïc Toupet, Cédric Fischmeister, Christophe M. Thomas and Jean-Luc Renaud
    Organometallics2010 29 (8), 1992-1995

    • New Dipyridylamine Ruthenium Complexes for Transfer Hydrogenation of Aryl Ketones in Water

      Charles Romain, Sylvain Gaillard, Mohammed K. Elmkaddem, Loïc Toupet, Cédric Fischmeister, Christophe M. Thomas and Jean-Luc Renaud
      Organometallics2010 29 (8), 1992-1995

      A new family of cationic organometallic chloro compounds of the type [(arene)Ru(N,N)(Cl)]+ containing N,N-chelating dipyridylamine ligands has been synthesized and isolated as the chloride salts, which are water soluble and stable to hydrolysis. The ...

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  • Published In Issue September 16, 2004
  • Received July 6, 2004

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