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1. Metal-free dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates.

Author

Chen, Xinyu, Yang, Na, Zeng, Wen, Wang, Lei, Li, Pinhua, and Li, Hongji

Subjects
*RING formation (Chemistry), *STERIC hindrance, *INDOLE
Abstract

Herein, we report a mild dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates. The unique [5+2] cycloaddition enables the synthesis of a series of dibenzo[b,e]azepine derivatives in moderate to good yields. Increasing the steric hindrance at the C2-position of 1H-indoles leads to the [2+2] cycloaddition. Mechanistic investigations support that the reaction of 1H-indoles with arynes undergoes a [2+2] cycloaddition step, followed by a ring expansion to the [5+2] cycloaddition product. [ABSTRACT FROM AUTHOR]

Published
2021
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