Popov Andrei G, Viviani Vincent R, Skumial Piotr, Jefferson Theodore L, Salman Samer G, Baxter Henry H, Hull Kami L
Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.
Org Lett. 2024 Jun 7;26(22):4621-4625. doi: 10.1021/acs.orglett.4c01198. Epub 2024 May 29.
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%.
本文介绍了1,5-铜催化的乙烯基环丙烷的碳胺化反应。由Cu(I)还原卤代烷形成的碳中心自由基加成到乙烯基环丙烷的烯烃上，引发开环生成苄基自由基，该自由基最终经过铜介导的胺化反应得到高烯丙基胺。该反应具有出色的区域选择性以及良好至非常好的非对映选择性。针对卤代烷、乙烯基环丙烷和胺亲核试剂这三种组分展示了该反应的适用范围。总共给出了38个例子，平均产率为60%。
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