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
Physical Sciences and Engineering (PSE) Division
Chemical Science Program
KAUST Catalysis Center (KCC)
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
Date
2015-08-17

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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.
Publisher
American Chemical Society (ACS)
Journal
Organic Letters
ISSN
1523-7060
1523-7052
DOI
10.1021/acs.orglett.5b01916
PubMed ID
26280104
Handle URI
http://hdl.handle.net/10754/575663
Is Supplemented By
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:http://hdl.handle.net/10754/624436
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:http://hdl.handle.net/10754/624472
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:http://hdl.handle.net/10754/624434
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:http://hdl.handle.net/10754/624435
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:http://hdl.handle.net/10754/624433
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