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.
TiO(acac)2 and VOCl2 are found to be environmentally friendly, water-tolerant, and easily recoverable catalysts. They allow efficient and chemoselective transesterification of methyl and ethyl esters as well as their conversion into amides and thioesters. A wide range of substrates reacts successfully and diverse functional groups are tolerated.
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