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Progress in Chemistry 2008, Vol. 20 Issue (12): 1909-1922 Previous Articles   Next Articles

• Review •

The Application of H-Cu-P Complexes in Organic Synthesis

Li Zhengning1* Liu Gailing1 Zhao Baoyi2   

  1. (1.Liaoning Key Laboratory of Bioorganic Chemistry, College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, China; 2. Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China)

  • Received: Revised: Online: Published:
  • Contact: Li Zhengning
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A survey of the literature up to Febrary 2008 on the progress of the preparation of [HCuPPh3]6 and the application of copper hydride-organo phosphine complexes in organic synthesis is presented in this article. As a reductant, [HCuPPh3]6 can selectively reduce the C=C double bond in α,β-unsaturated ester, ketone, aldehyde, nitro and nitrile compounds by hydrogen or silane. The C≡C triple bond in alkyne; as a catalyst, it can promote the reduction of C=C double bonds of aforementioned compounds by hydrogen or silane. The C=C double bond in these compounds or carbonyl group in α,β-unsaturated ketone and aldehyde, alkyl aryl and ketone can be selectively reduced by changing the phosphorous ligand. By employing suitable chiral phosphorous ligands, high enantioselective reductions of the C=C double bond, C=O double bond in prochiral substrates have been achieved. The special reactivity and catalytic activity have been utilized in the synthesis of structurally complex natural products and compounds of bioligical importance.

Key words: copper hydrides, Stryker’s reagents, phosphorous ligands, conjugated reduction, α,β- unsaturated compounds, asymmetric catalysis

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