Cyclic Hypervalent Iodine-Induced Oxidative Phenol and Aniline Couplings with Phenothiazines
Koji Morimoto, Kana Yanase, Kentaro Toda, Hitoshi Takeuchi, Toshifumi Dohi, Yasuyuki Kita
Abstract
C–H/N–H bond functionalization for direct intermolecular aryl C–N couplings is a useful synthetic process. In this study, we achieved metal-free cross-dehydrogenative coupling of phenols and anilines with phenothiazines using hypervalent iodine reagents. This method affords selective amination products under mild conditions. Electron-rich phenols and anilines could be employed, affording moderate-to-high yields of N-arylphenothiazines. Aniline amination proceeded efficiently at 20 °C, a previously unreported phenomenon.
Topics & Concepts
Hypervalent moleculeChemistryAnilineIodinePhenolOxidative phosphorylationCombinatorial chemistryOrganic chemistryBiochemistryOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsPhenothiazines and Benzothiazines Synthesis and Activities