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Metal-free dearomative [5+2]/[2+2] cycloaddition of 1H-indoles with ortho-(trimethylsilyl)aryl triflates.
- Source :
-
Chemical Communications . 7/21/2021, Vol. 57 Issue 57, p7047-7050. 4p. - Publication Year :
- 2021
-
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]
- Subjects :
- *RING formation (Chemistry)
*STERIC hindrance
*INDOLE
Subjects
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 57
- Issue :
- 57
- Database :
- Academic Search Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 151436565
- Full Text :
- https://doi.org/10.1039/d1cc02550c