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

Handle URI:
http://hdl.handle.net/10754/575663
Title:
Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction
Authors:
Chua, Ming Hui; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Xu, Jianwei; Wu, Jishan
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.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Chemical Science Program; Homogeneous Catalysis Laboratory (HCL)
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
Issue Date:
17-Aug-2015
DOI:
10.1021/acs.orglett.5b01916
Type:
Article
ISSN:
1523-7060; 1523-7052
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
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorChua, Ming Huien
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorXu, Jianweien
dc.contributor.authorWu, Jishanen
dc.date.accessioned2015-08-24T08:35:19Zen
dc.date.available2015-08-24T08:35:19Zen
dc.date.issued2015-08-17en
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.doi10.1021/acs.orglett.5b01916en
dc.identifier.urihttp://hdl.handle.net/10754/575663en
dc.description.abstractThe 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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleUnusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reactionen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)en
dc.identifier.journalOrganic Lettersen
dc.contributor.institutionInstitute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore, 117602, Singaporeen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singaporeen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByChua, 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/cc1j41qfen
dc.relation.isSupplementedByDOI:10.5517/cc1j41qfen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624436en
dc.relation.isSupplementedByChua, 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/cc1jr5wben
dc.relation.isSupplementedByDOI:10.5517/cc1jr5wben
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624472en
dc.relation.isSupplementedByChua, 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/cc1j41ncen
dc.relation.isSupplementedByDOI:10.5517/cc1j41ncen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624434en
dc.relation.isSupplementedByChua, 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/cc1j41pden
dc.relation.isSupplementedByDOI:10.5517/cc1j41pden
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624435en
dc.relation.isSupplementedByChua, 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/cc1j41mben
dc.relation.isSupplementedByDOI:10.5517/cc1j41mben
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624433en
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