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Issue 9, 2018
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Polyhedral Cu2O to Cu pseudomorphic conversion for stereoselective alkyne semihydrogenation

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Abstract

Cu2O cubes, octahedra, and rhombic dodecahedra can be pseudomorphically converted into Cu crystals of corresponding shapes through reduction by ammonia borane in ethanol at 50 °C or below within 3 min, demonstrating the feasibility of making challenging polyhedral metal particles from metal oxide crystals. Hydrogen gas is also produced from ammonia borane in the process. The obtained Cu crystals have a slightly nanoporous interior. Addition of diphenylacetylene in the formation of Cu rhombic dodecahedra leads to complete stereoselective production of sterically hindered (Z)-stilbene. Semihydrogenation of other alkynes also gives pure (Z)-alkenes. Cu cubes and octahedra also showed considerable (Z)-stilbene selectivity along with minor formation of (E)-stilbene and bibenzyl as compared to CuCl2 and commercial Cu2O particles. Mechanistic studies reveal that the low binding affinity of alkenes on the rhombic dodecahedra surfaces leads to high product selectivity. These Cu crystals act as a green and low-cost catalyst for the synthesis of high-purity (Z)-alkenes.

Graphical abstract: Polyhedral Cu2O to Cu pseudomorphic conversion for stereoselective alkyne semihydrogenation

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Publication details

The article was received on 10 Dec 2017, accepted on 29 Jan 2018 and first published on 31 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05232D
Citation: Chem. Sci., 2018,9, 2517-2524
  • Open access: Creative Commons BY license
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    Polyhedral Cu2O to Cu pseudomorphic conversion for stereoselective alkyne semihydrogenation

    S. Rej, M. Madasu, C. Tan, C. Hsia and M. H. Huang, Chem. Sci., 2018, 9, 2517
    DOI: 10.1039/C7SC05232D

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