Abstract
Regioselective benzannulation reaction of indol-3-yl-but-3-yn-2-ols to functionaly embellished 2-iodocarbazoles is described for the first time using iodine at room temperature in an open flask. This reaction proceeds through a cascade of 5-endo spirocyclization, ring-rearrangement through a vinyl shift, and aromatization in a short time. This protocol offers direct access to uncovered 2-iodocarbazoles, with a broad substrate scope and good to moderate yields. Further, we have demonstrated the synthetic potential of these compounds using cross-coupling reactions.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 6983-6988 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2019 |
| Issue number | 41 |
| DOIs | |
| State | Published - Nov 10 2019 |
| Externally published | Yes |
Bibliographical note
Funding Information:S. Y. is thankful for the financial support from CSIR (02/333/18/EMR‐II) India and SERB‐2016/4812. R. D. is thankful to SERB for the fellowship. We also acknowledge Dr Jovan Jose for his support for elucidating the mechanism.
Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- 2-Iodocarbazoles
- Benzannulation
- Cross-coupling
- Iodocyclization
- Reaction mechanisms