Efficient Metal-Free Oxidative C–H Amination for Accessing Dibenzoxazepinones via μ-Oxo Hypervalent Iodine Catalysis

Abstract

Dibenzoxazepinones exhibit unique biological activities and serve as building blocks for synthesizing pharmaceutical compounds. Despite remarkable advancements in organic chemistry and recent developments in synthetic approaches to dibenzoxazepinone motifs, there is a strong demand for more streamlined synthesis methods. The application of the catalytic C–H amination strategy, which enables the direct transformation of inert aromatic C–H bonds into C–N bonds, offers a rapid route to access dibenzoxazepinone frameworks. Hypervalent-iodine-catalyzed oxidative C–H amination has the potential to become an effective approach for synthesizing dibenzoxazepinones. In this study, we present our method of employing μ-oxo hypervalent iodine catalysis for intramolecular oxidative C–H amination of O-aryl salicylamides, facilitating the synthesis of target dibenzoxazepinone derivatives bearing various functional groups in a highly efficient manner.

Keywords

• μ-oxo hypervalent iodine
• oxidative C–H amination
• salicylamide
• dibenzoxazepinone
• greener organocatalysis