Visible-light-induced photocatalyst-free intramolecular sp3 C–H oxidation of 2‑alkyl benzamides. (28th September 2022)

• Record Type: Journal Article
• Authors: Wu, Lingang; Sun, Lei; Cui, Jichun; Xie, Lei; Wang, Yanlan; Nie, Shaozhen
• Is Part Of: Tetrahedron letters. Volume 107(2022)
• Publication Date: 2022-09-28
• Subjects: Hofmann–Löffler–Freytag (HLF) type reaction -- Amidyl radical -- Visible light photocatalysis -- 2‑Alkyl benzamides -- Photocatalyst-free; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154093
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A new amidyl radical-mediated intramolecular 2‑alkyl benzamide oxidation reaction was developed under mild photochemical conditions. This Hofmann–Löffler–Freytag (HLF) type reaction involved the formation of intramolecular sp 3 CO bonds via a different pathway than the construction of CN bonds in classic and modified HLF reactions. The oxidation proceeded smoothly at room temperature without any photocatalyst, and the desired products were provided in moderate to excellent yields with exclusive chemoselectivity.