芳炔是一类重要的活性有机中间体，在杂环合成和天然产物合成中都有着广泛的应用。本项目在前期芳炔环加成反应和Baylis-Hillman反应两部分工作的基础上，进一步对芳炔与BH反应产物的选择性环加成反应开展研究。采用插入-环化串联反应策略，利用氮杂BH产物、BH产物及其衍生物与芳炔的环加成反应构筑苯并杂环类化合物。通过对BH产物结构、电性以及空间位阻等因素的调节，并结合Lewis酸等添加剂，实现对这类芳炔环加成反应化学选择性和立体选择性的有效调控。解决这类杂环合成中存在的反应步骤复杂、反应条件苛刻以及底物和官能团兼容性较差等问题，发展温和条件下，非金属催化"一步法"合成多官能团化四氢喹啉、苯并四氢吡喃等氮、氧杂环及其衍生物的简洁方法。通过该项目的实施，发展新的杂环合成方法学，同时可以促进芳炔化学和杂环合成化学的发展。

Arynes are highly reactive intermediates that used widely in heterocycle synthesis and natural product synthesis.In this project, based on our previous work on aryne chemistry and Baylis-Hillman reaction,the selective cycloaddition of arynes and Baylis-Hillman adducts will be investigated. Using bond-insertion strategy, aza-Baylis-Hillman adducts, Baylis-Hillman adducts as well as their derivatives can react with arynes to construct benzoheterocycles. The chemo- and stereoselectivity can be manipulated by modifying the steric and electronic properties of Baylis-Hillman adducts with assistance of Lewis acid.A series of problems that exist in the synthesis of benzoheterocycles,such as multi-step reaction,harsh reaction conditions,limited scope of substrates and functional group will be solved. Meanwhile, a mild, conscious and transition-metal-free protocol for the synthesis of tetrahydroquinoline,tetrahydrobenzo[b]pyran and other nitrogen or oxygen-containing heterocycles will be developed. Through the implementation of this project, new method for the synthesis of benzoheterocycles will be developed, which will push the progress of aryne chemistry as well as heterocyclic chemistry.