From ynamides to highly substituted benzo[b]furans

• Verfasst von: Blanco Jaimes, Maria Camila [VerfasserIn]
• Verfasst von: Claus, Vanessa [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: From ynamides to highly substituted benzo[b]furans
• Titelzusatz: gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates
• Verf.angabe: Maria Camila Blanco Jaimes, Vanessa Weingand, Frank Rominger, and A. Stephen K. Hashmi
• E-Jahr: 2013
• Jahr: August 6, 2013
• Umfang: 8 S.
• Teil: volume:19
• Teil: year:2013
• Teil: number:37
• Teil: pages:12504-12511
• Teil: extent:8
• Fussnoten: Gesehen am 30.04.2021
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2013
• Band/Heft Quelle: 19(2013), 37, Seite 12504-12511
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201301595
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: From ynamides to highly substituted benzo[b]​furans. - 2013
• Sach-SW: cyclization
• Sach-SW: gold
• Sach-SW: heterocycles
• Sach-SW: rearrangement
• Sach-SW: ynamides
• K10plus-PPN: 1756666261

Abstract

A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both CO and CC formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process.