Direct photoassisted α-Trifluoromethylation of aromatic Ketones with trifluoroacetic Anhydride (TFAA)

• Verfasst von: Das, Somnath [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Schaub, Thomas [VerfasserIn]
• Titel: Direct photoassisted α-Trifluoromethylation of aromatic Ketones with trifluoroacetic Anhydride (TFAA)
• Verf.angabe: Somnath Das, A. Stephen K. Hashmi, and Thomas Schaub
• Jahr: 2019
• Umfang: 5 S.
• Fussnoten: First published: 03 December 2018 ; Gesehen am 01.03.2019
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Ort Quelle: Weinheim : Wiley-VCH, 2001
• Jahr Quelle: 2019
• Band/Heft Quelle: 361(2019), 4, Seite 720-724
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201801305
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Aromatic ketone
• Sach-SW: Fluorinated organic compounds
• Sach-SW: Photoredox catalysis
• Sach-SW: Trifluoroacetic anhydride
• Sach-SW: Trifluoromethylation
• K10plus-PPN: 1588263428

Abstract

Direct α-Trifluoromethylation of acetophenone derivatives was achieved by using trifluoroacetic anhydride (TFAA) as the trifluoromethyl source and pyridine-N-oxide (Py−O) as activator and oxidant under visible light irradiation and tris-(2,2′-bipyridine)ruthenium(II) hexafluorophosphate (Ru(bpy)3(PF6)2) as the photocatalyst. Different acetophenone derivatives could be converted to the corresponding α-CF3 derivatives with high selectivity. Extensive mechanistic investigation revealed the formation of vinyl trifluoroacetate as the key intermediate for this transformation.