Cyclic Hypervalent Iodine-Induced Oxidative Phenol and Aniline Couplings with Phenothiazines

C-H/N-H bond functionalization for direct inter-molecular 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 degrees C, a previously unreported phenomenon.

Automated summary

In this study, a metal-free cross-dehydrogenative coupling of phenols and anilines with phenothiazines was achieved using hypervalent iodine reagents. The method allowed selective amination products to be obtained under mild conditions. The reaction proceeded efficiently at previously unreported 20 degrees C for aniline amination.