Cheng Yuan LiuTaveechai WititsuwannakulChu Han HsiehChung Yu TsaiTing Hsuan WangRam AmbreWen Ching ChenPanida SurawatanawongTiow Gan OngNational Taiwan University of Science and TechnologyMahidol UniversityNational Chiao Tung University TaiwanAcademia Sinica, Institute of Chemistry2020-01-272020-01-272019-01-01Journal of the Chinese Chemical Society. (2019)21926549000945362-s2.0-85077850258https://repository.li.mahidol.ac.th/handle/20.500.14594/50595© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.Mahidol UniversityChemistryConference PaperSCOPUS10.1002/jccs.201900450