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Updated: May 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-Catalyzed Allylic Amination of Alkenes Using O-Acylhydroxylamines: A Direct Entry to Diverse N-Alkyl
Eric J McLaren1, Guangshou Feng1, Noah H Watkins1
1Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.
Abstract:
We report a copper-catalyzed direct allylic amination of alkenes using readily available O-benzyolhydroxylamines as the alkylamine precursors and internal oxidant. A range of primary and secondary alkylamines can be installed onto diversely substituted alkenes for rapid construction of N-alkyl allylamines. Mechanistic studies support that the reaction engages an initial electrophilic amination to alkenes with anti-Markovnikov selectivity and subsequently a regioselective oxidative elimination to furnish the double bond transposition. In the electrophilic amination step, the use of strong Brønsted acid is critical for generating the key aminium radical cation (ARC) species.
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