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

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
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)