Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes,Organic Letters

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Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes
Organic Letters ( IF 4.9 ) Pub Date : 2020-10-19 , DOI: 10.1021/acs.orglett.0c02988
Jonathan J Kennedy-Ellis ₁ , Erik D Boldt ₁ , Sherry R Chemler ₁

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A direct assembly of secondary benzylureas and related amine derivatives via copper-catalyzed carboamination of styrenes with potassium alkyltrifluoroborates and ureas, anilines, or an amide is reported. Terminal and 1,2-disubstituted alkenes, as well as dienes, participate in this three-component coupling reaction. The reaction mechanism likely involves the addition of an alkyl radical to the styrene, followed by metal-mediated oxidative coupling of the resulting benzylic radical with the amine derivative. Factors that impact substrate reactivity and regioselectivity are discussed.

中文翻译：

铜催化苯乙烯三组分碳胺化合成苄脲类及相关胺类衍生物

据报道，通过铜催化的苯乙烯与烷基三氟硼酸钾和尿素、苯胺或酰胺的碳胺化，直接组装仲苄基脲和相关的胺衍生物。末端和 1,2-二取代的烯烃以及二烯烃参与了这种三组分偶联反应。反应机制可能涉及向苯乙烯添加烷基，然后是金属介导的苄基自由基与胺衍生物的氧化偶联。讨论了影响底物反应性和区域选择性的因素。

更新日期：2020-11-06

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