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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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
07 January 2025
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| In: |
Chemistry - a European journal
Year: 2025, Volume: 31, Issue: 13, Pages: 1-9 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202404170 |
| Online Access: | 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 
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| Author Notes: | Jonas F. Wunsch, Hendrick M. Sommer, Senta J. Kohl, Rouven Maier, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
| Summary: | 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. |
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| Item Description: | Veröffentlicht: 07. Januar 2025 Gesehen am 07.04.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202404170 |