On the gold-catalyzed generation of phenyl cations from 1,5-Diynes

• Verfasst von: Wurm, Thomas [VerfasserIn]
• Verfasst von: Bucher, Janina [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: On the gold-catalyzed generation of phenyl cations from 1,5-Diynes
• Verf.angabe: Thomas Wurm, Janina Bucher, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
• Umfang: 6 S.
• Fussnoten: Gesehen am 28.08.2017
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Jahr Quelle: 2017
• Band/Heft Quelle: 359(2017), 10, S. 1637-1642
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201700231
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562772368

Abstract

cis-Enediyne systems bearing two non-terminal alkyne functionalities were transformed in the presence of a gold catalyst. A selective 6-endo-dig-cyclization generates mono-aurated phenyl cation intermediates, high energy species that are able to activate even primary sp3-C-H-bonds. Via insertion into intramolecularly offered, unactivated C-H-bonds, penta-substituted benzene derivatives are obtained as final products. In most cases selective insertions into the γ-sp3-C—H bonds of the offered tethers were observed.