Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides
Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides
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DOI：
10.1021/jacs.8b11942
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发表时间：
2018-12-26
影响因子：
15
通讯作者：
Engle, Keary M.
中科院分区：
文献类型：
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作者：
Derosa, Joseph;Kleinmans, Roman;Engle, Keary M.
报道了镍催化的简单烯基酰胺与芳基碘和芳基硼酸酯的联合偶联反应。该反应通过缺电子烯烃（EDO）配体富马酸二甲酯实现，并以优异的区域控制提供所需的1，2-二芳基化产物。在优化的条件下，广泛的酰胺衍生自3-丁烯酸，4-戊烯酸，和烯丙基胺是相容的底物。该方法代表了由天然酰胺官能团指导的区域控制的1，2-二芳基化的第一个实例。计算分析揭示了潜在的底物结合模式和EDO配体在还原消除步骤中的作用。
A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocon-trolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.