Gold‐Catalyzed One‐Pot Cycloisomerization/Nucleophilic Addition/Rearrangement of Acenaphthylene Carbaldehyde Derivatives
Abstract: Merging the latest advances in the field of gold catalysis and the efficiency of hexafluoro‐2‐propanol (HFIP), a gold‐catalyzed orthogonal tandem reaction has been developed to access carbocyclic ketone on naphthalene substrates. The methodology involved a cycloisomerization/nucleophilic addition and a C→O rearrangement. The HFIP solvent most probably acted as a Lewis‐acid on isochromene derivatives, through hydrogen donor bond activity. A large range of acenaphthylene carbaldehyde has been engaged in this process coupling gold catalysis and Lewis‐acid behavior of HFIP leading to cyclic ketones with a yield ranging from 15 to 91% (27 compounds). The mechanism was investigated, and the reaction most presumably occurred via a classical cyclization process followed by a [Au]‐HFIP interaction for the final rearrangement. The interest of such transformation was demonstrated by performing it on a gram‐scale. Moreover, a post‐functionalization bromination was performed, as well as the isomerization of some functionalized ketones leading to full trans derivatives with a yield ranging from 78 to 90% yields.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Gold‐Catalyzed One‐Pot Cycloisomerization/Nucleophilic Addition/Rearrangement of Acenaphthylene Carbaldehyde Derivatives ; day:28 ; month:02 ; year:2023 ; extent:8
Advanced synthesis & catalysis ; (28.02.2023) (gesamt 8)
- Creator
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Truchon, Alexis
Dupeux, Aurélien
Olivero, Sandra
Michelet, Véronique
- DOI
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10.1002/adsc.202201387
- URN
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urn:nbn:de:101:1-2023030114094212868076
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:48 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Truchon, Alexis
- Dupeux, Aurélien
- Olivero, Sandra
- Michelet, Véronique
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