1,3-偶极化合物与有机硼化合物的非金属催化反应研究

The common reactions with 1,3-dipoles are 1,3-dipolar cycloaddtion with dipolarophiles, as well as nucleophilic addition reactions to the unsaturated bonds. This study systematically explores the reactions of 1,3-dipoles with organoboron compounds to make full use of their electrophilicity and nucleophilicity, based on the special structures. This study achieves the addition reaction of organoboron compounds with 1,3-dipoles in metal-free conditions via coordination-migration process. This study also explores a series of migration groups, including carbon, nitrogen, boron and phosphorus, as well as indicates the universal 1,4-migaration process. This study will develop a new type of reaction to synthesize many valuable products, such as functionalized nitrogen-containing compounds from the reaction of organoboron compounds with allyl anion type 1,3-dipoles, carbonyl compounds from the reaction of boronic acids with propargyl anion type 1,3-dipoles.

1,3-偶极化合物常见的反应是与亲偶极子的1,3-偶极环加成反应，以及对其不饱和键的亲核加成反应。本项目从1,3-偶极化合物的特殊结构出发，充分利用其亲电和亲核的性质，系统探索1,3-偶极化合物与有机硼化合物偶联反应。本项目探索在非金属催化的条件下，通过1,3-偶极化合物与有机硼化合物的配位-迁移反应，实现有机硼化合物对1,3-偶极化合物的加成反应。本项目研究拓展一系列的迁移基团，包括碳、硼、硅和膦等，与此同时也说明了1,4-迁移过程的普适性。本项目拟发展一类新方法可以用于合成多种有价值的产物：有机硼化合物与烯丙基离子型1,3-偶极化合物反应生成多种官能团化的含氮化合物、有机硼酸与炔丙基离子型1,3-偶极化合物反应生成羰基化合物。