Efficient difunctionalization of alkenes allows the rapid construction of molecular complexity from simple building blocks in organic synthesis. We present herein a nickel-catalyzed dicarbofunctionalization of alkenes using readily available organoboronic acids and organic halides in a three-component fashion. In particular, an unprecedented regioselectivity of the 1,3-dicarbofunctionalization of N-allylpyrimidin-2-amine is achieved when aryl and methyl iodides are utilized. In contrast, the use of alkyl bromides with β-hydrogens results in 1,3-hydroarylation or oxidative 1,3-diarylation. Preliminary mechanistic studies suggest an isomerization involving nickel hydride in the 1,3-difunctionalization reactions. On the other hand, the use of alkenyl or alkynyl halides promotes alternative regioselectivities to deliver 1,2-alkenylcarbonation or intriguing 2,1-alkynylcarbonation products. Such 2,1-alkynylarylation is also applicable to N-allylbenzamide as a different class of substrates. Overall, this nickel-catalyzed process proves to be powerful in delivering versatile difunctionalized compounds using readily available reagents/catalysts and a simple procedure.

中文翻译：

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使用具有不同区域选择性的有机硼酸和卤化物进行镍催化的烯丙基部分的双官能化

烯烃的有效双官能化可以从有机合成中的简单结构单元快速构建分子复杂性。我们在本文中以三组分方式使用容易获得的有机硼酸和有机卤化物，对烯烃进行镍催化的双碳官能化。尤其是N的1,3-二糖官能化的前所未有的区域选择性当使用芳基和甲基碘时，可以得到-烯丙基嘧啶-2-胺。相反，将烷基溴化物与β-氢一起使用会导致1,3-氢芳基化或氧化1,3-二芳基化。初步的机理研究表明，在1,3-双官能化反应中涉及氢化镍的异构化反应。另一方面，烯基或炔基卤化物的使用促进了选择性的区域选择性，以递送1，2-烯基碳酸化或吸引人的2，1-炔基碳酸化产物。这样的2，1-炔基芳基化也可以作为不同种类的底物应用于N-烯丙基苯甲酰胺。总的来说，使用容易获得的试剂/催化剂和简单的方法，这种镍催化的方法在提供通用的双官能化化合物方面非常有效。