Gold catalysis

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Häffner, Tobias [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: Gold catalysis
• Titelzusatz: domino reaction of en-diynes to highly substituted phenols
• Verf.angabe: A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger
• E-Jahr: 2011
• Jahr: 07 June 2011
• Umfang: 7 S.
• Fussnoten: Gesehen am 31.08.2022
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2011
• Band/Heft Quelle: 17(2011), 29, Seite 8195-8201
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201100305
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: Gold catalysis. - 2011
• Sach-SW: alkynes
• Sach-SW: domino reactions
• Sach-SW: furans
• Sach-SW: gold
• Sach-SW: phenols
• K10plus-PPN: 1815457708

Abstract

By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substituted phenols in an efficient domino reaction. Furan derivatives were formed as intermediates; this was proven by in situ NMR spectroscopy. The uncommon substitution pattern of these furans opens the way for a selective formation of phenols that contain the hydroxyl group in the meta position to the ring junction, which previously was not possible by gold-catalyzed furan-yne cyclization. Furthermore, interesting mechanistic insights were obtained by products derived from secondary allyl alcohols. In this case, in addition to the phenolic compounds, a ketone is formed by 1,2-alkyl shift.