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

Ming Hui Chua; Kuo-Wei Huang; Jianwei Xu; Jishan Wu

doi:10.1021/acs.orglett.5b01916

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

Ming Hui Chua, Kuo-Wei Huang, Jianwei Xu, Jishan Wu

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4168-4171
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.5b01916
State	Published - Aug 17 2015

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

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.",

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T1 - Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction

AU - Chua, Ming Hui

AU - Huang, Kuo-Wei

AU - Xu, Jianwei

AU - Wu, Jishan

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2015/8/17

Y1 - 2015/8/17

N2 - 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.

AB - 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.

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DO - 10.1021/acs.orglett.5b01916

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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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CCDC 1404072: Experimental Crystal Structure Determination : difluoro(2-((pentafluorophenyl)(5-(triphenylvinyl)-2H-pyrrol-2-ylidene)methyl)-5-(triphenylvinyl)-1H-pyrrolato)borate

CCDC 1404071: Experimental Crystal Structure Determination : 5,5-difluoro-10-phenyl-3-(1,2,2-triphenylethyl)-7-(triphenylvinyl)-5H-4lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1404073: Experimental Crystal Structure Determination : difluoro(2-((pentafluorophenyl)(5-(1,2,2-triphenylethyl)-2H-pyrrol-2-ylidene)methyl)-5-(triphenylvinyl)-1H-pyrrolato)borate

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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

Abstract

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Datasets

CCDC 1404072: Experimental Crystal Structure Determination : difluoro(2-((pentafluorophenyl)(5-(triphenylvinyl)-2H-pyrrol-2-ylidene)methyl)-5-(triphenylvinyl)-1H-pyrrolato)borate

CCDC 1404071: Experimental Crystal Structure Determination : 5,5-difluoro-10-phenyl-3-(1,2,2-triphenylethyl)-7-(triphenylvinyl)-5H-4lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1404073: Experimental Crystal Structure Determination : difluoro(2-((pentafluorophenyl)(5-(1,2,2-triphenylethyl)-2H-pyrrol-2-ylidene)methyl)-5-(triphenylvinyl)-1H-pyrrolato)borate

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