Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction
Type
ArticleKAUST Department
Chemical Science ProgramChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2015-08-17Online Publication Date
2015-08-17Print Publication Date
2015-09-04Permanent link to this record
http://hdl.handle.net/10754/575663
Metadata
Show full item recordAbstract
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 LettersPubMed ID
26280104Relations
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
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