The gold-catalyzed hydroarylation of alkynes with electron-rich heteroarenes

• Verfasst von: Schießl, Jasmin [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: The gold-catalyzed hydroarylation of alkynes with electron-rich heteroarenes
• Titelzusatz: a kinetic investigation and new synthetic possibilities
• Verf.angabe: Jasmin Schießl, Matthias Rudolph, A. Stephen K. Hashmi
• Umfang: 15 S.
• Fussnoten: Gesehen am 22.08.2017
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Jahr Quelle: 2017
• Band/Heft Quelle: 359(2017), 4, S. 639-653
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201600940
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562613510

Abstract

The gold-catalyzed mono-hydroarylation and two-fold hydroarylation of alkynes with electron-rich heteroarenes was analyzed by a 1H NMR kinetic study. The obtained rate constants for the decreasing alkyne concentration provide information on the reactivity of this addition reaction. The examinations show the orthogonal reactivity of gold and a proton for the two reaction steps. The first hydroarylation is exclusively promoted by gold(I), whereas the second step is premised on a proton which will be reversibly derived from the formation of σ,π-acetylide complexes from the terminal alkynes or by interaction with solvents. Based on kinetic data, it was possible to synthesize a large range of mono-adducts in moderate to good yields, furthermore the synthesis of hetero-di-adducts, bearing two different substituents, was explored.