文献类型：期刊文献

英文题名：Recent advances in oxidative dearomatization involving C-H bonds for constructing value-added oxindoles

作者：Yu, Le-Mao[1,3];Chen, Haojin[2];Fang, Wenjing[2];Cai, Ruonan[2];Tao, Yi[2];Li, Yong[2];Dong, Huaping[3]

机构：[1]Zhejiang Univ, Coll Chem & Biol Engn, Hangzhou 310018, Peoples R China;[2]Shaoxing Univ, Sch Chem & Chem Engn, Shaoxing 312000, Peoples R China;[3]Shaoxing Univ, Green Pharmaceut & Proc Res Ctr, Shaoxing 312000, Peoples R China

年份：2024

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：SCI-EXPANDED(收录号：WOS:001293030600001)、、EI(收录号：20243516938618)、Scopus(收录号：2-s2.0-85201859682)、WOS

基金：We thank the National Natural Science Foundation of China (no. 21677101) and Zhejiang Provincial Department of Education Project (no. Y202248434) for financial support. We thank the reviewers for their helpful comments and suggestions.

语种：英文

外文摘要：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. The present review highlights the dearomatization of indoles by oxidizing C-H bonds for constructing oxindoles skeletons. Various synthetic approaches have been summarized followed by their applications in indole alkaloids and bioactive compounds.