Radical cascade silylation/cyclization of 1,7-dienes to access silyl-substituted benzo[b]azepin-2-ones.

Zhen Zhang,Lichao Lu,Guiling Li, Xiaoyu Sheng, Yijia Zhang, Lin Yang,Jiaqi Zhao,Lei Xie,Jiazhu Li, Kai Sun

Chemical communications (Cambridge, England)(2024)

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Abstract
A novel silyl radical-induced cascade silylation/cyclization of 1,7-dienes has been realized employing readily available hydrosilanes as a silicon source and Cu(I) salt as a catalyst. This protocol introduces diverse silicon fragments into a challenging 7-membered ring structure and provides an efficient approach to a wide array of biologically important silyl-substituted benzo[b]azepin-2-ones. Several control experiments suggest that the reaction undergoes a free radical process. The gram-scale synthesis and late-stage transformations further demonstrate the scalability and applicability of the reaction in organic synthesis.
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