One step synthesis of 4,6,8-Trimethoxyazulenes: as building block for 2-functionalized azulenes
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselect...
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| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
07 January 2025
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| In: |
Chemistry - a European journal
Year: 2025, Jahrgang: 31, Heft: 13, Pages: 1-9 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202404170 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202404170 Verlag, kostenfrei, Volltext: https://www.webofscience.com/api/gateway?GWVersion=2&SrcAuth=DOISource&SrcApp=WOS&KeyAID=10.1002%2Fchem.202404170&DestApp=DOI&SrcAppSID=EUW1ED0F7Foi9lcejdJw9hzzgfZIn&SrcJTitle=CHEMISTRY-A+EUROPEAN+JOURNAL&DestDOIRegistrantName=Wiley+%28John+Wiley+%26+Sons%29 |
| Verfasserangaben: | Jonas F. Wunsch, Hendrick M. Sommer, Senta J. Kohl, Rouven Maier, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
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| 245 | 1 | 0 | |a One step synthesis of 4,6,8-Trimethoxyazulenes |b as building block for 2-functionalized azulenes |c Jonas F. Wunsch, Hendrick M. Sommer, Senta J. Kohl, Rouven Maier, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
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| 520 | |a Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives. | ||
| 650 | 4 | |a 1,3-DIYNES | |
| 650 | 4 | |a 2-SUBSTITUTED AZULENES | |
| 650 | 4 | |a Azulene | |
| 650 | 4 | |a BASIS-SETS | |
| 650 | 4 | |a DERIVATIVES | |
| 650 | 4 | |a E-Z-isomerization | |
| 650 | 4 | |a Electrophilic aromatic substitution | |
| 650 | 4 | |a ELECTROPHILIC SUBSTITUTION | |
| 650 | 4 | |a EXPANSION-ANNULATION STRATEGY | |
| 650 | 4 | |a Gold catalysis | |
| 650 | 4 | |a LIGANDS | |
| 650 | 4 | |a REACTIVITY | |
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| 650 | 4 | |a SUBSTITUTED AZULENES | |
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