Access to Azepino-Annulated Benzo[ c]carbazoles Enabled by Gold-Catalyzed Hydroarylation of Alkynylindoles and Subsequent Oxidative Cyclization

Org Lett. 2022 Sep 16;24(36):6505-6509. doi: 10.1021/acs.orglett.2c02293. Epub 2022 Sep 1.

Abstract

Herein, we report a facile and efficient synthetic method to construct azepino[1,2-a]indoles through a novel gold(I)-catalyzed intramolecular hydroarylation of alkynylindoles. A wide range of functional groups can be well tolerated in this transformation, and the corresponding highly functionalized azepino[1,2-a]indole skeletons were obtained in moderate to excellent yields. Subsequent oxidation of the products gave the interesting and valuable polycyclic carbazoles, which were widely used as the key building blocks in materials science.