標題: Nickel-mediated cross-coupling via C-O activation assisted by organoaluminum
作者: Liu, Cheng-Yuan
Wititsuwannakul, Taveechai
Hsieh, Chu-Han
Tsai, Chung-Yu
Wang, Ting-Hsuan
Ambre, Ram
Chen, Wen-Ching
Surawatanawong, Panida
Ong, Tiow-Gan
應用化學系
Department of Applied Chemistry
公開日期: 1-一月-1970
摘要: 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 degrees 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 beta-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.
URI: http://dx.doi.org/10.1002/jccs.201900450
http://hdl.handle.net/11536/153645
ISSN: 0009-4536
DOI: 10.1002/jccs.201900450
期刊: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
起始頁: 0
結束頁: 0
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