Gold catalysis

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Littmann, Anna Christina [VerfasserIn]
• Titel: Gold catalysis
• Titelzusatz: one-pot alkylideneoxazoline synthesis/alder-ene reaction
• Verf.angabe: A. Stephen K. Hashmi and Anna Littmann
• E-Jahr: 2012
• Jahr: 20 March 2012
• Umfang: 8 S.
• Fussnoten: Gesehen am 06.09.2018
• Titel Quelle: Enthalten in: Chemistry
• Ort Quelle: Weinheim : Wiley-VCH, 2006
• Jahr Quelle: 2012
• Band/Heft Quelle: 7(2012), 6, Seite 1435-1442
• ISSN Quelle: 1861-471X
• DOI: doi:10.1002/asia.201200046
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: Hashmi, A. Stephen K., 1963 - : Gold catalysis: one-pot alkylideneoxazoline synthesis, Alder-ene reaction. - 2012
• Sach-SW: alkynes
• Sach-SW: amides
• Sach-SW: gold
• Sach-SW: heterocycles
• Sach-SW: oxazoles
• K10plus-PPN: 1580751741

Abstract

Based on the gold-catalyzed synthesis of methyleneoxazolines, a one-pot combination with an Alder-ene reaction was developed. For azodicarboxylates, good to very good yields (51-99 %) of the oxazolemethylhydrazinedicarboxylates were achieved with 3 mol % of the Gagosz catalyst, [Ph3PAuNTf3]. In a less-selective reaction, 4-phenyl-3H-1,2,4-triazol-3,5(4 H)-dione gave lower yields (41-49 %) of the corresponding oxazolemethylphenyltriazolidinediones. Overall, five new bonds were formed. Tetracyanoethylene afforded a cyclobutane derivative through a [2+2] cycloaddition reaction at −40 °C, but only 45 % of the spiro compound was obtained. The less-readily available KITPHOS ligands on gold gave even higher yields at lower catalyst loadings (2 mol %), but longer reaction times were required.