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Palladium-Catalyzed Intramolecular Heck Dearomative Alkenylation of Indoles with N-Tosylhydrazones
- Source :
- The Journal of Organic Chemistry; August 2022, Vol. 87 Issue: 16 p10917-10927, 11p
- Publication Year :
- 2022
-
Abstract
- An elegant Pd-catalyzed intramolecular Heck dearomative alkenylation of aryl iodides with functionalized N-tosylhydrazones proceeded through a sequential dearomative carbopalladation, migratory insertion, and β-hydride elimination in the presence of Pd(CF3COO)2(10 mol %), PPh3(30 mol %), and Cs2CO3(2.0 equiv) in 1,4-dioxane (2.0 mL) at 120 °C for 14 h under an argon atmosphere. This cascade cycloaddition protocol provided a reliable and versatile approach to a sequence of structurally diverse indolines in moderate to good yields with good functional group compatibility. In addition, the synthetic robustness of the methodology is highlighted by a scaled-up experiment and derivatization of products via epoxidation and reduction reactions.
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 87
- Issue :
- 16
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs60592888
- Full Text :
- https://doi.org/10.1021/acs.joc.2c01209