C-H键活化是当前有机化学领域的研究热点之一。过渡金属催化的基于C-H键活化的C-H/C-H交叉偶联反应是形成碳-碳键的最直接和有效途径，内烯烃烯基C-H/C-H的氧化(脱氢)偶联是一个具有挑战性的课题。本申请课题利用给电子/吸电子取代基的push-pull效应活化内烯烃烯基C-H键的策略，设计与合成S,N-取代的极化内烯烃底物、重组高效的过渡金属催化剂体系，在相对温和的条件下进行内烯烃烯基C-H/C-H(或N-H)的氧化偶联(串联)反应。主要研究吲哚、吡咯酮、氮杂双环化合物和喹啉衍生物等氮杂环体系的骨架构建、研究所得氮杂环产物经由过渡金属催化C-S键断裂与有机硼酸偶联的进一步官能团化以及与肼、羟胺或胍等缩合的衍生化。探索相关反应机理与规律，由此发展多取代(高度官能团化)氮杂环化合物的有机合成新方法学，推动绿色有机合成化学的发展。

C-H activation is one of the present hot topics in organic chemistry. Transition metal-catalyzed C-H/C-H cross-coupling is considered as the most promising and concise route to a C-C bond, and oxidative C-H/C-H coupling involving internal olefinic C-H bonds is a challenging task for organic chemists. We will develop a strategy to activate internal olefinic C-H bonds by means of the push-pull effect of the substituents on a C=C bond, that is, introducing two electron-donating functionalities such as a thioalkyl and an alkyl- or arylamino group, and an electron-withdrawing moiety to the two ends of the target C=C bond. In this manner, the olefin is tuned polarized to make its olefinic C-H activated. Under the optimal conditions, transition metal-catalyzed oxidative C-H/C-H (or N-H) cross-coupling will be investigated to construct the backbones of indole, pyrrolone, aza-bicycle, and quinoline derivatives. Further transformations of the resultant products will be carried out by transition metal-catalyzes C-S cleavage with organic boronic acids, and condensation with hydrazines, hydroxylamine, and guanidines. The reaction mechanisms will also be explored. Thus, new synthetic methodologies for the synthesis of multisubstituted (highly functionalized) N-heterocyclic compounds will be established, contributing our efforts to the progress in green chemistry.