Copper-Catalyzed Three-Component Carboiminolactonization of Electron-Deficient Olefins.
Copper-Catalyzed Three-Component Carboiminolactonization of Electron-Deficient Olefins.
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DOI：
10.1021/acs.joc.3c02326
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发表时间：
2024-01
期刊：
影响因子：
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通讯作者：
Hanna Wendlandt;G. Trammel;Daniel G Kohler;Jacob A Utley;Aja M Nicely;Andrei G Popov;Kami L. Hull
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文献类型：
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作者：
Hanna Wendlandt;G. Trammel;Daniel G Kohler;Jacob A Utley;Aja M Nicely;Andrei G Popov;Kami L. Hull
本文报道了三组分铜催化的α，β-不饱和羰基衍生物的亚胺羰基内酯化反应。在Cu（I）催化剂的存在下，α-卤代酯、缺电子烯烃和伯胺在单一步骤中偶联生成γ-亚氨基内酯。反应的范围进行了探讨相对于三个耦合合作伙伴。19个例子，这些水解不稳定的杂环的产率高达69%。机理研究支持通过原子转移自由基加成（ATRA）中间体形成氧代碳正离子。
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.