有机硼化合物在现代物质科学的诸多领域，应用非常广泛。虽然其制备方法已有许多报道，但是，开发高效、环保、经济的合成方法，仍然是合成化学领域一个充满挑战的课题。本项目拟开发新的反应体系，探索硼自由基的新反应性能，研究它们与贫电子不饱和烃类的特异α−加成反应，为构建结构多元的α-硼取代分子寻找新的合成路径。我们也将探索不对称自由基反应，以制备光学纯的α-硼取代产物。同时，我们将深入探究反应机理，弄清控制α-选择性和立体选择性的决定因素，进一步揭示硼自由基的反应本质。此外，我们也将研究硼化产物在合成化学，以及药物分子后期修饰等方面的应用。亲核性自由基物种与贫电子不饱和烃一般发生β-加成反应，然而，亲核性的硼自由基则发生α-加成反应。弄清该逆向区域选择性的本质，具有十分重要的科学意义。本项目的成功实施，不仅可以为有机硼化合物的制备开辟新路径，而且也将进一步完善自由基反应的基础理论，促进该领域的发展。

Organoboron compounds have been widely applied in modern chemical society. Although many borylation methods have been reported, the exploration of new reactions that can lead to more efficient, environmentally friendly, and economic synthetic approaches represents a highly important yet challenging goal in synthetic chemistry. In this project, we aim to explore new reactivity of boryl radicals towards unusual α−addition to electron-poor alkenes and alkynes, from which versatile α−borylated functionalized products would be constructed. Meanwhile, we will establish new strategies that can enable asymmetric radical additions to afford enantioenriched organoboron compounds. We will perform detailed mechanistic studies to elucidate the factors that control the α−selectivity and stereoselectivity, and thus to further disclose the nature of boryl radicals. In addition, the synthetic applications of the organoboron products would be demonstrated in the modification of drug molecules and natural products, as well as in photolectric materials. Generally, nucleophilic radical species undergo β−additions to electron poor alkenes and alkynes, due to strong inductive effect, while nucleophlic boryl radicals perform specific α−addition instead. To elucidate the factors that control this unusual regioselectivity would be of great significance and value in both theoretical and synthetic chemistry. The implementation of this project would provide new methods to access organoboron compounds, meanwhile it would also be able to complement the basic theory of radical reaction, and thus to boost the development of radical chemistry society.