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Title: Nickel-mediated cross-coupling via C–O activation assisted by organoaluminum
Authors: Cheng Yuan Liu
Taveechai Wititsuwannakul
Chu Han Hsieh
Chung Yu Tsai
Ting Hsuan Wang
Ram Ambre
Wen Ching Chen
Panida Surawatanawong
Tiow Gan Ong
National Taiwan University of Science and Technology
Mahidol University
National Chiao Tung University Taiwan
Academia Sinica, Institute of Chemistry
Keywords: Chemistry
Issue Date: 1-Jan-2019
Citation: Journal of the Chinese Chemical Society. (2019)
Abstract: © 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.
ISSN: 21926549
Appears in Collections:Scopus 2019

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