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    Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

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    Type
    Article
    Authors
    Jia, Weiguo
    Li, Dandan
    Dai, Yuanchen
    Zhang, Hui
    Yan, Liqin
    Sheng, Enhong
    Wei, Yun
    Mu, Xiaolong
    Huang, Kuo-Wei cc
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2014
    Permanent link to this record
    http://hdl.handle.net/10754/563220
    
    Metadata
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    Abstract
    Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2] (3) (Dm-Pybox = 2,6-bis[4′,4′- dimethyloxazolin-2′-yl]pyridine) were obtained by reactions of CuX 2 (X = Cl, Br) with DMOX and Dm-Pybox ligands, respectively. The molecular structures of 1, 2 and 3 have been determined by single-crystal X-ray diffraction analyses. The complexes 2 and 3 are efficient in catalyzing α-amination of ketones and esters through α-bromo carbonyl intermediate. The procedures are environmentally benign methods using molecular oxygen as an oxidant with water as the only byproduct. This journal is © the Partner Organisations 2014.
    Citation
    Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). Synthesis and characterization of bisoxazolines- and pybox-copper(ii) complexes and their application in the coupling of α-carbonyls with functionalized amines. Org. Biomol. Chem., 12(29), 5509–5516. doi:10.1039/c4ob01027b
    Sponsors
    This work was supported by the National Nature Science Foundation of China (21102004), and the Natural Science Foundation of the Anhui Higher Education Institutions of China (KJ2011A146), and the Project-sponsored by SRF for ROCS, SEM. K.-W. Huang acknowledges financial support from KAUST. We also thank Dr Richmond Lee for English polishing.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Organic & Biomolecular Chemistry
    DOI
    10.1039/c4ob01027b
    Relations
    Is Supplemented By:
    • [Dataset]
      Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973033: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj5d. DOI: 10.5517/cc11nj5d HANDLE: 10754/624286
    • [Dataset]
      Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 973034: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11nj6f. DOI: 10.5517/cc11nj6f HANDLE: 10754/624287
    • [Dataset]
      Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 978999: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11vqm7. DOI: 10.5517/cc11vqm7 HANDLE: 10754/624301
    • [Dataset]
      Jia, W.-G., Li, D.-D., Dai, Y.-C., Zhang, H., Yan, L.-Q., Sheng, E.-H., … Huang, K.-W. (2014). CCDC 981179: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc11xzyw. DOI: 10.5517/cc11xzyw HANDLE: 10754/624303
    ae974a485f413a2113503eed53cd6c53
    10.1039/c4ob01027b
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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