Wendlandt Hannah C, Trammel Grace L, Kohler Daniel G, Utley Jacob A, Nicely Aja M, Popov Andrei G, Hull Kami L
Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
J Org Chem. 2024 Feb 2;89(3):2024-2031. doi: 10.1021/acs.joc.3c02326. Epub 2024 Jan 10.
Herein we report the three-component copper-catalyzed carboiminolactonization of α,β-unsaturated carbonyl derivatives. In the presence of a Cu(I) catalyst, α-haloesters, electron-deficient alkenes, and primary amines couple to generate γ-iminolactones in a single step. The scope of the reaction is explored with respect to the three coupling partners. Nineteen examples are presented with yields of these hydrolytically labile heterocycles of up to 69%. Mechanistic investigations support the formation of an oxocarbenium by way of an atom transfer radical addition (ATRA) intermediate.
在此，我们报道了α,β-不饱和羰基衍生物的三组分铜催化碳亚胺内酯化反应。在Cu(I)催化剂存在下，α-卤代酯、缺电子烯烃和伯胺发生偶联，一步生成γ-亚胺内酯。针对三种偶联反应物对反应范围进行了探索。给出了19个例子，这些水解不稳定杂环的产率高达69%。机理研究支持通过原子转移自由基加成(ATRA)中间体形成氧鎓碳正离子。
