We report the alkylation and arylation cross‐coupling of aryl ethers based on C–O bond activation using a nickel catalyst and organoaluminum reagents. Ni(cod)₂ in combination with 1,2‐bis(dicyclohexylphosphino)ethane ligand in toluene solution at 130°C are the best conditions. The naphthyl ether or methoxy pyridine derivatives are suitable substrates for alkylation and arylation reaction with a wider scope of aluminum reagents in good yields. Computational analysis on the pyridine substrate is provided to help delineate the mechanistic pathway and demonstrate the important aspects of the cooperative interaction bimetallic catalysis. First, the coordination of AlMe₃ to the O atom of pyridine is essential for C–O activation. Second, the β‐H transfer from methoxy to pyridine could be discouraged through the use of bidentate phosphine as a ligand. Finally, excess AlMe₃ reagent is critical for facilitating a reductive elimination process.

中文翻译：

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通过有机铝辅助的C–O活化进行的镍介导的交叉偶联

我们报告了使用镍催化剂和有机铝试剂基于C–O键活化的芳基醚的烷基化和芳基化交叉偶联。Ni（cod）₂与1,2-双（二环己基膦基）乙烷配体在130°C的甲苯溶液中结合是最佳条件。萘醚或甲氧基吡啶衍生物是适合烷基化和芳基化反应的底物，可以与更大范围的铝试剂以高收率进行反应。提供了对吡啶底物的计算分析，以帮助描绘机理途径，并证明了协同相互作用双金属催化的重要方面。一，AlMe ₃的协调吡啶O原子上的碳原子对于C–O活化至关重要。其次，可以通过使用双齿膦作为配体来阻止从甲氧基到吡啶的β-H转移。最后，过量的AlMe ₃试剂对于促进还原消除过程至关重要。