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Aryne-mediated [2,3]-sigmatropic rearrangement of tertiary 2,3-allenylamines bearing an electron-withdrawing group at the α-position
- Source :
- Organicbiomolecular chemistry. 19(24)
- Publication Year :
- 2021
-
Abstract
- An unprecedented [2,3]-sigmatropic rearrangement reaction of quaternary 2,3-allenylammonium ylides, generated in situ from tertiary 2,3-allenylamines and arynes, has been established. With 2-(trimethylsilyl)aryl triflates as aryne precursors, a range of tertiary 2,3-allenylamines bearing an electron-withdrawing group at the α-position smoothly participated in the aryne-mediated [2,3]-sigmatropic rearrangement at room temperature, delivering structurally diverse 2-vinylallyamines or 1-amino-1,3-dienes in moderate to excellent yields. The reaction proceeds in the absence of strong bases and transition metals, is compatible with moisture and air, and tolerates a wide variety of functional groups.
Details
- ISSN :
- 14770539
- Volume :
- 19
- Issue :
- 24
- Database :
- OpenAIRE
- Journal :
- Organicbiomolecular chemistry
- Accession number :
- edsair.doi.dedup.....e4ad2082c29ff7a266495b49fe30038f