烯烃或炔烃等不饱和烃的氢芳基化反应具有高原子经济性、步骤经济性的特点，被认为是构建碳-碳键的最有效途径之一。有机硼试剂由于具有过渡金属催化的特质，近年来被广泛应用于氢化、硅氢化、硼化等反应，然而其在氢芳基化反应方面的研究鲜有报道。本项目拟以硼路易斯酸为催化剂，在我们前期硼催化1,3-共轭二烯的氢芳基化反应的工作基础上，通过量子化学计算结合实验研究，系统研究烯烃氢芳基化反应机理，阐明底物对活化模式及区域选择性的影响；深入考察不同硼路易斯酸催化剂的反应效率及其影响因素；在反应机理和催化剂效率研究的基础上，利用自动化反应路径搜索程序理论评估新反应底物，包括惰性烯烃、炔烃、联烯等不饱和烃的反应活性，筛选出潜在可行的反应体系，并实验验证。项目拟采用理论模拟先行，实验验证与其相互反馈验证的策略，力争建立硼催化的高效、高选择性氢芳基化反应体系，为构建碳-碳键提供新的策略。

Hydroarylation reaction of alkenes or alkynes is considered as one of the most efficient method for the C−C bond-forming reaction, due to its high atom and step economy. Over the past decade, Organoboron compounds has demonstrated extensive applications in a wide variety of reactions, including hydrogenation, borylation and hydrosilylation. However, the borane-catalyzed hydroarylation reaction has been rarely reported so far. In this project, based on our preliminary results on borane-catalyzed hydroarylation of 1,3-conjugated dienes with phenols, we plan to investigate the detailed mechanism of hydroarylation of alkenes and the role of substrates on the activation mode and selectivity via a combination of quantum chemical calculations and experimental studies. Additionally, the catalytic efficiency of different boron-catalysts will also be thoroughly investigated. On the basis of mechanism and catalyst efficiency investigations, we will further investigate the reactivity of other substrates, including unactivated alkenes, alkynes and allenes. The reactivity of these substrates will be evaluated and screened first using the automatic reaction path search program, and then verified by experimental studies. These works will establish an efficient and highly selective borane-catalyzed hydroarylation reaction system, and provide a new strategy for the carbon-carbon bond-forming reactions.