Photosensitizer-free visible-light-mediated gold-catalyzed 1,2-difunctionalization of alkynes

• Verfasst von: Huang, Long [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Photosensitizer-free visible-light-mediated gold-catalyzed 1,2-difunctionalization of alkynes
• Verf.angabe: Long Huang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
• Umfang: 6 S.
• Fussnoten: Gesehen am 29.09.2017
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Jahr Quelle: 2016
• Band/Heft Quelle: 55(2016), 15, S. 4808-4813
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201511487
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Parallele Sprachausgabe deutsch: Huang, Long: Gold-katalysierte 1,2-Difunktionalisierung von Alkinen mit sichtbarem Licht ohne zusätzlichen Photosensibilisator
• K10plus-PPN: 1563971208

Abstract

Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional-group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one-pot processes. With a P,N-bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex.