Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Häffner, Tobias [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes
• Verf.angabe: A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger
• E-Jahr: 2011
• Jahr: February 2011
• Jahr des Originals: 2010
• Umfang: 5 S.
• Illustrationen: Illustrationen
• Fussnoten: First published: 27 December 2010 ; Gesehen am 31.08.2022
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Ort Quelle: Weinheim : Wiley-VCH Verl., 1998
• Jahr Quelle: 2011
• Band/Heft Quelle: (2011), 4, Seite 667-671
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/ejoc.201001479
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes. - 2011
• Sach-SW: Allylic compounds
• Sach-SW: Carbene ligands
• Sach-SW: Cycloisomerization
• Sach-SW: Gold
• Sach-SW: Oxygen heterocycles
• K10plus-PPN: 181552846X

Abstract

Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI catalysts bearing carbene ligands, of either the N-heterocyclic carbene or nitrogen acyclic carbene type, delivered the desired products with low catalyst loadings and under very mild reaction conditions. A broad array of substrates was tested, including alkyl-, alkenyl-, and aryl-substituted alkynes, as well as substrates with two alkynyl moieties. The methodology turned out to have a broad scope. Secondary allyl alcohols were also tolerated, and the resulting trisubstituted furans could be isolated in high yields.