A new N-iodosuccinimide-mediated intramolecular oxidation to construct C−O bonds has been developed. The reaction differs in the construction of the C−N bond from the classic and modified Hofmann-Löffler-Freytag reactions.
In this work, we describe the N-iodosuccinimide-mediated benzyl sp3 C−H oxidation of 2-alkyl-substituted benzamide derivatives. This Hofmann-Löffler-Freytag (HLF) type reaction involving intramolecular sp3 C−O bond formation differs from the construction of the C−N bond in the classic and modified HLF reactions. This reaction proceeded smoothly via 1,5-hydrogen atom transfer of N-centered radicals directly afforded by in situ N−I bond generation, providing iminoisobenzofuran derivatives in moderate to excellent yields with exclusive chemoselectivity.Zum Volltext