Mechanochemical solvent-less cross-couplings have emerged as a powerful frontier in the formation of carbon–carbon and carbon–heteroatom bonds under sustainable conditions. However, despite considerable progress, mechanochemical decarbonylative cross-couplings have been unexplored. Herein, we report the first decarbonylative mechanochemical cross-coupling for the heteroarylation of amides by a triple C–N/C–C/C–H activation. The catalytic system exploits cooperative Ni/Cu catalysis to simultaneously activate the amide N–C(O) and the heterocycle C–H bonds, resulting in a highly chemoselective coupling. The reaction is characterized by a broad scope of the amide and the heterocyclic component to furnish heterobiaryls, which are among the most privileged scaffolds in organic synthesis. We demonstrate that decarbonylative mechanochemical cross-couplings will provide novel access to a range of valuable products that are among the most common structures in organic chemistry.

中文翻译：

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通过协同催化和三重 C-N/C-C/C-H 活化实现酰胺的机械化学脱羰基交叉偶联


机械化学无溶剂交叉偶联已成为在可持续条件下形成碳-碳和碳-杂原子键的强大前沿。然而，尽管取得了相当大的进展，但机械化学脱羰基交叉偶联仍未得到探索。在此，我们报道了通过三重 C-N/C-C/C-H 活化实现酰胺杂芳化的第一个脱羰基机械化学交叉偶联。该催化系统利用协同 Ni/Cu 催化同时激活酰胺 N-C（O） 和杂环 C-H 键，从而产生高化学选择性偶联。该反应的特点是酰胺和杂环组分的广泛范围以提供异联芳基，这是有机合成中最优越的支架之一。我们证明，脱羰基机械化学交叉偶联将为一系列有价值的产品提供新的途径，这些产品是有机化学中最常见的结构之一。