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    Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction

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    Type
    Article
    Authors
    Chua, Ming Hui
    Huang, Kuo-Wei cc
    Xu, Jianwei
    Wu, Jishan
    KAUST Department
    Chemical Science Program
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2015-08-17
    Online Publication Date
    2015-08-17
    Print Publication Date
    2015-09-04
    Permanent link to this record
    http://hdl.handle.net/10754/575663
    
    Metadata
    Show full item record
    Abstract
    The straightforward synthesis of 3,5-di(triphenylethylenyl) BODIPYs 1–3 from the condensation of 2-(triphenylethylenyl) pyrrole with aryl aldehydes are surprisingly found to produce side products that are hydrogenated at one of the two triphenylethylene substituents. It was also observed that the subsequent Scholl type reaction of 1 resulted in a “1,2-migratory shift” of one triphenylethylene substituent in addition to a ring closing reaction. Preliminary investigations, including DFT calculations and isolation of intermediates, were conducted to study these unusual observations on BODIPY chemistry.
    Citation
    Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction. Organic Letters, 17(17), 4168–4171. doi:10.1021/acs.orglett.5b01916
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/acs.orglett.5b01916
    PubMed ID
    26280104
    Relations
    Is Supplemented By:
    • [Dataset]
      Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). CCDC 1404074: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1j41qf. DOI: 10.5517/cc1j41qf HANDLE: 10754/624436
    • [Dataset]
      Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). CCDC 1422462: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1jr5wb. DOI: 10.5517/cc1jr5wb HANDLE: 10754/624472
    • [Dataset]
      Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). CCDC 1404072: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1j41nc. DOI: 10.5517/cc1j41nc HANDLE: 10754/624434
    • [Dataset]
      Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). CCDC 1404073: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1j41pd. DOI: 10.5517/cc1j41pd HANDLE: 10754/624435
    • [Dataset]
      Chua, M. H., Huang, K.-W., Xu, J., & Wu, J. (2015). CCDC 1404071: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1j41mb. DOI: 10.5517/cc1j41mb HANDLE: 10754/624433
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.orglett.5b01916
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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