Gold-catalysis

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Yang, Weibo [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: Gold-catalysis
• Titelzusatz: highly efficient and regio-selective carbonyl migration in alkynyl-substituted indole-3-carboxamides leading to azepino[3,4-b]indol-1-ones
• Verf.angabe: A. Stephen K. Hashmi, Weibo Yang, and Frank Rominger
• E-Jahr: 2012
• Jahr: April 24, 2012
• Umfang: 7 S.
• Fussnoten: Gesehen am 06.09.2018
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Ort Quelle: Weinheim : Wiley-VCH, 2001
• Jahr Quelle: 2012
• Band/Heft Quelle: 354(2012), 7, Seite 1273-1279
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201200092
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: acylamino migration
• Sach-SW: alkynes
• Sach-SW: gold
• Sach-SW: heterocycles
• Sach-SW: indoles
• K10plus-PPN: 1580754279

Abstract

An unprecedented rearrangement/anellation sequence allows the clean synthesis of azepino[3,4-b]indol-1-ones from readily available starting materials. Alkyne-substituted indole-3-carboxamides were prepared and converted to azepino[3,4-b]indol-1-ones by the SPhosAuNTf2 catalyst (SPhos=2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl). The new connectivity, which involves an unprecedented 3,2-shift of an acylamino group for the product formation, was proven by a crystal structure analysis.