Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different productsElectronic supplementary information (ESI) available: Copies of 1H, 13C, and 19F NMR, HRMS, UV-vis and fluorescence spectra. See DOI: 10.1039/c5nj00808e
An efficient synthesis of 3-fluoroterrylene, a promising molecular nanoprobe for single electron optical sensing, is described. The key synthetic steps comprised the palladium-catalysed cross-coupling reaction of 3-bromoperylene and 4-fluoronaphthalene-1-boronic acid pinacol ester to give 3-(4-fluoronaphthalen-1-yl)perylene, followed by oxidative cyclodehydrogenation to give selectively either 3-fluoroterrylene or its isomer 10-fluorobenzo[4,5]indeno[1,2,3- cd ]perylene. The selectivity of the Scholl oxidation under AlCl 3 /chlorobenzene or DDQ/TfOH conditions was confirmed by 19 F NMR. Oxidative cyclodehydrogenation of 3-(4-fluoronaphthalen-1-yl)perylene gives, by reaction with AlCl 3 , 3-fluoroterrylene and by reaction with DDQ/TfOH, its isomer 10-fluorobenzo[4,5]indeno[1,2,3- cd ]perylene..
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2015 |
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| Erschienen: |
2015 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:39 |
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| Enthalten in: |
New journal of chemistry - 39(2015), 8, Seite 6498-653 |
| Beteiligte Personen: |
Markoulides, Marios S [VerfasserIn] |
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| Links: |
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| doi: |
10.1039/c5nj00808e |
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| 245 | 1 | 0 | |a Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different productsElectronic supplementary information (ESI) available: Copies of 1H, 13C, and 19F NMR, HRMS, UV-vis and fluorescence spectra. See DOI: 10.1039/c5nj00808e |
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| 520 | |a An efficient synthesis of 3-fluoroterrylene, a promising molecular nanoprobe for single electron optical sensing, is described. The key synthetic steps comprised the palladium-catalysed cross-coupling reaction of 3-bromoperylene and 4-fluoronaphthalene-1-boronic acid pinacol ester to give 3-(4-fluoronaphthalen-1-yl)perylene, followed by oxidative cyclodehydrogenation to give selectively either 3-fluoroterrylene or its isomer 10-fluorobenzo[4,5]indeno[1,2,3- cd ]perylene. The selectivity of the Scholl oxidation under AlCl 3 /chlorobenzene or DDQ/TfOH conditions was confirmed by 19 F NMR. Oxidative cyclodehydrogenation of 3-(4-fluoronaphthalen-1-yl)perylene gives, by reaction with AlCl 3 , 3-fluoroterrylene and by reaction with DDQ/TfOH, its isomer 10-fluorobenzo[4,5]indeno[1,2,3- cd ]perylene. | ||
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