Recent advances in oxidative dearomatization involving C–H bonds for constructing value-added oxindoles

Abstract

Exploring three-dimensional chemical space is an important research objective of organic synthetic chemistry. Oxidative dearomatization (ODA) is one of the most important and powerful tools for realizing this goal, because it changes and removes aromatic structures from aromatic compounds to increase levels of saturation and stereoisomerism by direct addition reactions between functional groups with aromatic cores under oxidative conditions. As a hot topic in indole chemistry, the synthetic value of the oxidative dearomatization of indoles has been well recognized and has witnessed rapid development recently, since it could provide convenient and unprecedented access to fabricate high-value-added three-dimensional oxindole skeletons, such as C-quaternary indolones, polycycloindolones and spiroindolones, and be widely applied to the total synthesis of these oxindole alkaloids. Therefore, this article provides a review of recent developments in oxidative dearomatization involving the C–H bonds of indoles. In this article, the features and mechanisms of different types of ODA reactions of indoles are summarized and represented, and asymmetric synthesis methods and their applications are illustrated with examples, and future development trends in this field are predicted at the end.