Dual gold catalysis

• Verfasst von: Bucher, Janina [VerfasserIn]
• Verfasst von: Wurm, Thomas [VerfasserIn]
• Verfasst von: Taschinski, Svenja [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Dual gold catalysis
• Titelzusatz: synthesis of fluorene derivatives from diynes
• Verf.angabe: Janina Bucher, Thomas Wurm, Svenja Taschinski, Eleni Sachs, David Ascough, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
• Jahr des Originals: 2016
• Umfang: 9 S.
• Fussnoten: Online published: 8 December 2016
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Jahr Quelle: 2017
• Band/Heft Quelle: 359(2017), 2, S. 225-233
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201600987
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562589016

Abstract

1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)-H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield.