铜催化缺电子烯烃的三组分碳胺化反应
Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins.
作者信息
Nicely Aja M, Popov Andrei G, Wendlandt Hannah C, Trammel Grace L, Kohler Daniel G, Hull Kami L
机构信息
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States.
Department of Chemistry, University of Illinois Urbana-Champaign, Urbana, Illinois 61812, United States.
出版信息
Org Lett. 2023 Jul 21;25(28):5302-5307. doi: 10.1021/acs.orglett.3c01866. Epub 2023 Jul 13.
Abstract
The copper-catalyzed three-component carboamination of atropates for the synthesis of α-aryl amino acid derivatives is presented. The scope of the reaction is explored with respect to all three coupling partners: the alkyl halide, the atropate, and the aryl amine. A total of 41 examples are included, with yields of ≤92%. Both primary and secondary aryl amines participate in the carboamination along with α-haloesters, nitriles, and perfluoroiodoalkanes. Mechanistic investigations support a radical mechanism involving Cu-mediated C-N bond formation with the radical adduct.
摘要
本文介绍了用于合成α-芳基氨基酸衍生物的铜催化的阿卓酸酯三组分碳胺化反应。针对所有三种偶联伙伴：卤代烃、阿卓酸酯和芳基胺，对该反应的范围进行了探索。总共包括41个例子，产率≤92%。伯芳基胺和仲芳基胺均与α-卤代酯、腈和全氟碘代烷一起参与碳胺化反应。机理研究支持一种自由基机理，该机理涉及铜介导的与自由基加合物形成C-N键。
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