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Updated: Jun 25, 2025

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Published on: May 26, 2019
Copper-Catalyzed Three-Component 1,5-Carboamination of Vinylcyclopropanes
Andrei G Popov1, Vincent R Viviani1, Piotr Skumial1
1Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.
Abstract:
The 1,5-copper-catalyzed carboamination of vinylcyclopropanes is presented. A carbon-centered radical, formed upon reduction of an alkyl halide by Cu(I), adds across the alkene of a vinylcyclopropane, triggering ring opening to generate a benzylic radical, which, finally, undergoes copper-mediated amination to afford a homoallylic amine. The reaction occurs with outstanding regio- and good to very good diastereoselectivities. The scope of the reaction is demonstrated with respect to all three components: alkyl halide, vinylcyclopropane, and amine nucleophile. A total of 38 examples are presented with an average yield of 60%.
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