Catalytic methods that transform C−H bonds into C−X bonds are of paramount importance in synthesis. A particular focus has been the generation of organoboranes, organosilanes and organostannanes from simple hydrocarbons (X=B, Si, Sn). Despite the importance of organozinc compounds (X=Zn), their synthesis by the catalytic functionalisation of C−H bonds remains unknown. Herein, we show that a palladium catalyst and zinc hydride reagent can be used to transform C−H bonds into C−Zn bonds. The new catalytic C−H zincation protocol has been applied to a variety of arenes—including fluoroarenes, heteroarenes, and benzene—with high chemo‐ and regioselectivity. A mechanistic study shows that heterometallic Pd–Zn complexes play a key role in catalysis. The conclusions of this work are twofold; the first is that valuable organozinc compounds are finally accessible by catalytic C−H functionalisation, the second is that heterometallic complexes are intimately involved in bond‐making and bond‐breaking steps of C−H functionalisation.

中文翻译：

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芳烃的钯催化CH键镀锌：范围，机理和杂金属中间体的作用

将CH键转换为X键的催化方法在合成中至关重要。特别关注的是由简单的烃类（X = B，Si，Sn）生成有机硼烷，有机硅烷和有机锡烷。尽管有机锌化合物（X = Zn）的重要性，但它们通过CH键的催化功能化合成的方法仍然未知。在这里，我们表明钯催化剂和氢化锌试剂可用于将CH键转换为CH键。新的CH-H催化锌化方案已应用于具有高化学和区域选择性的多种芳烃（包括氟芳烃，杂芳烃和苯）。机理研究表明，Pd-Zn杂金属配合物在催化中起关键作用。这项工作的结论是双重的。