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Directed Copper-Catalyzed Intermolecular Aminative Difunctionalization of Unactivated Alkenes
- Source :
- Journal of the American Chemical Society; November 2019, Vol. 141 Issue: 46 p18475-18485, 11p
- Publication Year :
- 2019
-
Abstract
- A diverse collection of copper-catalyzed intermolecular aminative difunctionalizations of unactivated alkenes with N-halodialkylamines as the terminal dialkylamino source is reported. A bidentate auxiliary tethered on the alkene substrates is crucial, which can promote the migratory insertion of nonactivated alkenes into the aminyl radical–metal complex and stabilize the resultant high-valent copper intermediate to allow for further transformations. By employing this strategy, the intermolecular aminohalogenation reactions and a three-component aminoazidation reaction of unactivated alkenes with dialkylamino source were successively achieved in a remarkable regio- and stereoselective manner. These reactions were performed under neutral conditions and maintained excellent functional group tolerance toward a wide range of N-halodialkylamines and unactivated alkenes. Further mechanistic studies and DFT calculations supported a concerted migratory insertion of the C–C double bond into the aminyl radical–metal complex to form a Cu(III) intermediate.
Details
- Language :
- English
- ISSN :
- 00027863 and 15205126
- Volume :
- 141
- Issue :
- 46
- Database :
- Supplemental Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Periodical
- Accession number :
- ejs51163637
- Full Text :
- https://doi.org/10.1021/jacs.9b07607