亚胺通过碱促进的C-H Borylation反应合成1,2-硼氮杂萘

介绍一条高产率通过苄基亚胺合成1,2-硼氮杂萘的新路线。

Synthesis of 1,2-Borazaronaphthalenes from Imines by Base-Promoted Borylation of C–H bond

Xinwang Liu , Pengbo Wu , Jianfeng Li , and Chunming Cui *

State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Cooperative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People’s Republic of China

J. Org. Chem

A new route from benzylic imines permits the synthesis of 1,2-borazaronaphthalenes in good yields. The reaction involves formation of the enamidyl dibromoborane, which undergoes base-promoted borylation of the nearby aromatic C–H bond. Electrophilic attack of the boron species onto the benzylic arene is supported by the slow borylation of arenes substituted with electron-withdrawing groups. The resultant boron bromides can be easily substituted with lithium reagents to provide a range of products. The electronic properties of these 1,2-borazaronaphthalene derivatives have been investigated by UV–vis and fluorescence spectroscopy.