Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks
Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks
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DOI：
10.1002/anie.201913062
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发表时间：
2019-12-12
影响因子：
16.6
通讯作者：
Engle, Keary M.
中科院分区：
文献类型：
--
作者：
Derosa, Joseph;Kang, Taeho;Engle, Keary M.
报道了镍催化的烯基羧酸、芳基碘和芳基/烯基硼酸酯的联合交叉偶联反应。该反应以优异的区域控制提供所需的1，2-二芳基化和1，2-芳基烯基化产物。为了证明该方法的合成效用，以克规模制备代表性产物，然后使用双电子和单电子逻辑将其多样化为8个1，2，3-三官能化结构单元。使用该方法，在产率和/或步数方面改进了朝向生物活性分子的三条路线。该方法代表了由天然羧酸酯基团引导的烯烃的催化1，2-二芳基化的第一个实例。
A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate group.