Chan–Evans–Lam偶联反应为构建碳氮键的重要方法之一，双亲核试剂的化学选择性Chan–Evans–Lam偶联反应可为复杂含氮化合物的快速构建提供便捷路径。以本课题组前期开发的化学选择性碳氮偶联反应为基础，本项目拟对该类反应的反应机理进行系统研究，并在此基础上设计实施双亲核试剂与不同种类芳基硼试剂的多组分反应，实现化学专一性的连续碳氮键偶联反应。具体研究内容包括：（1）利用动力学研究和密度泛函理论计算研究铜催化下的Chan–Evans–Lam偶联反应机理，阐明双亲核试剂参与的化学选择性碳氮偶联的反应性差异的根源；（2）探索催化剂、配体、反应溶剂等实验变量最佳组合，实现两种芳基硼试剂与含有两个氨基位点的双亲核试剂的高效多组分反应，实现反应中四个亲核位点的高选择性连接。项目进行中，机理研究将为实验方案的改进和修正提供理论指导，实验产生的新反应性也将为机理研究指明新的目标。

The Chan–Evans–Lam coupling reaction is one of the important methods to construct C–N bonds. Chemoselective Chan–Evans–Lam reactions between di-nucleophilic reagents and aryl boron species can provide a convenient pathway for the rapid construction of complex nitrogen-containing compounds. Based on chemoselective oxidative C–N coupling reactions, which were previously developed by our group, this project intends to systematically study the reaction mechanism of this kind of reactions. We also plan to design and implement the multi-component reaction among di-nucleophilic reagents and different aryl boron species, to realize the tandem construction of C–N bonds with high chemoselectivity. The research contents will include: (1) Mechanism of the Cu-catalyzed Chan–Evans–Lam coupling will be investigated based on kinetic research and Density Functional Theory calculations, and explanation will be made to describe the origin of observed chemoselectivity in experiments between di-nucleophilic reagents and aryl boron species; (2) Experiments will be carried out to explore the best combination of reaction variables such as catalysts, ligands and solvents, to realize the chemoselective multi-component reaction among two aryl boron reagents and di-nucleophilic reagents containing two amino groups. The four nucleophilic positions will be connected with high orthogonal chemoselectivity. In this project, the mechanism research will provide theoretical guidance for the improvement and correction of the experimental plans, and the new reactivity observed during the experiments will also indicate a new goal for the mechanism research.