【作者】 王立；

【导师】 雷爱文； 张华；

【作者基本信息】 南昌大学 ， 化学， 2021， 硕士

【摘要】 碳碳键断裂在石油工业和复杂有机分子合成中有着非常广泛的应用。碳碳键断裂可以使得利用自然界和化学工业中广泛且廉价的原材料来直接生产高附加值功能化合物成为可能。在过去的几十年中,碳碳键活化得到了快速发展,包括通过环张力释放实现张力碳碳键活化,以及通过氧化加成(腈和酮),β-碳消除(醇,胺和其他底物),氧化和其他途径实现极性碳碳键活化。然而非极性非张力碳碳键活化仅有极少量的报道,并主要局限于过渡金属催化的含两个导向基团化合物的氢化裂解反应。本论文首先论述了不同类型碳碳键活化反应。在之前工作的基础上,通过硼酸三甲酯促进的断裂硼化反应策略实现非极性非张力碳碳键活化。论文的主要研究成果如下:1.以廉价易得的硼酸三甲酯为催化剂,实现了2-甲基吲哚化合物与联硼酸频那醇酯的C2位选择性碳碳键断裂硼化反应,并对底物范围进行了拓展。2.以当量硼酸三甲酯为促进剂,实现了2-烷基吲哚化合物或2-芳基吲哚化合物与联硼酸频那醇酯的C2位选择性碳碳键断裂硼化反应,并对底物范围进行了拓展,对该反应的机理进行了详细研究。更多还原

【Abstract】 Carbon-carbon bond cleavage has a wide range of applications in important industrial processes,e.g.in the petroleum chemistry,and in complex molecule synthesis.It enables the direct production of valuable functionalized products from widely available and inexpensive raw materials from nature resources and the chemical industry.In recent decades,the rapid development of methods for C–C bond activation has enabled cleavage of C–C bonds in strained systems via strain release,and of polar C–C bonds via oxidative addition（nitriles and ketones）,b-carbon elimination（alcohols,amines and other substrates）,oxidation,and other pathways.In contrast,non-polar unstrained C–C bond activation is still a major challenge and reported examples are rare.Current strategies for non-polar unstrained C–C bond activation mainly focus on transition-metal-catalysed reductive hydrogenolysis of substrates bearing two ortho directing groups.This thesis first discusses the different types of carbon-carbon bond activation reactions.Based on previous work,the activation of non-polar unstrained C–C bond is achieved by the fracture boronization reaction strategy promoted by B（OMe）₃.The main research results of the thesis are as follows:1.Using cheap and easily available B（OMe）₃ as a catalyst,the C2-selective carbon-carbon bond scission boronization reaction of 2-methylindole compound and B₂pin₂ was realized,and the range of substrates was expanded.2.With the equivalent of B（OMe）₃ as the accelerator,the selective carbon-carbon bond scission borylation reaction of 2-alkylindole compound or2-arylindole compound and B₂pin₂ at C2 was realized,and The range of substances has been expanded,and the mechanism of the reaction has been studied in detail.更多还原