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Issue 10, 2013
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Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines

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Abstract

A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au–Pd alloy catalysts (Au–Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.

Graphical abstract: Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines

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Publication details

The article was received on 11 Jun 2013, accepted on 02 Aug 2013 and first published on 06 Aug 2013


Article type: Communication
DOI: 10.1039/C3GC41117F
Citation: Green Chem., 2013,15, 2680-2684
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    Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines

    L. Zhang, W. Wang, A. Wang, Y. Cui, X. Yang, Y. Huang, X. Liu, W. Liu, J. Son, H. Oji and T. Zhang, Green Chem., 2013, 15, 2680
    DOI: 10.1039/C3GC41117F

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