State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China.
Nat Commun. 2021 May 24;12(1):3070. doi: 10.1038/s41467-021-23371-x.
The construction of 7-membered ring via direct C7-H cyclization of benzoimidazoles with alkenes would provide a more atom- and step-economical route to tricyclic imidazoles and derivatives that widely exist in a broad range of bioactive molecules. However, transition metal-catalyzed C-H cyclization for medium-ring synthesis has been limited to reactive C-H bonds, instead, the activation of unreactive C-H bonds towards medium synthesis still remains an elusive challenge. Herein, we report a direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C7-H cyclization of benzoimidazoles with alkenes, providing a series of tricyclic imidazoles in 40-98% yield and with up to 95:5 er.
通过苯并咪唑与烯烃的直接 C7-H 环化构建 7 元环，为三环咪唑及其衍生物的合成提供了一条更原子经济性和步骤经济性的路线，这些衍生物广泛存在于各种生物活性分子中。然而，过渡金属催化的中环合成 C-H 环化仅限于反应性 C-H 键，相反，对中环合成的非反应性 C-H 键的激活仍然是一个难以捉摸的挑战。在此，我们报告了通过 Ni-Al 共催化苯并咪唑与烯烃的非活性 C7-H 环化，直接构建 7 元环，以 40-98%的产率和高达 95:5 的对映选择性得到一系列三环咪唑。
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