Qiao Li, Zhang Ke, Wang Zhichao, Li Hanjie, Lu Ping, Wang Yanguang
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
J Org Chem. 2021 Jun 18;86(12):7955-7962. doi: 10.1021/acs.joc.1c00186. Epub 2021 Jun 1.
A visible-light-promoted aerobic hydroxyazidation of indole derivatives with TMSN is described. The reaction proceeded under photocatalyst-free conditions to furnish -2-azidoindolin-3-ols with high regioselectivity and stereoselectivity. The protocol is operationally simple, and the starting materials (e.g., 1-(pyrimidin-2-yl) indoles, azidotrimethylsilane, and air) are readily available. The proposed mechanism in which substrates act as photocatalysts upon excitation using blue light-emitting diodes (LEDs) was supported by experimental studies.
本文描述了一种可见光促进的吲哚衍生物与三甲基硅基叠氮化物的需氧羟基叠氮化反应。该反应在无光催化剂的条件下进行，以高区域选择性和立体选择性提供 -2-叠氮基吲哚啉-3-醇。该方法操作简单，起始原料（如1-(嘧啶-2-基)吲哚、叠氮基三甲基硅烷和空气）易于获得。实验研究支持了所提出的机制，即在使用蓝色发光二极管（LED）激发时，底物充当光催化剂。
