Publication: Nickel-mediated cross-coupling via C–O activation assisted by organoaluminum
1
Issued Date
2019-01-01
Resource Type
ISSN
21926549
00094536
00094536
Other identifier(s)
2-s2.0-85077850258
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of the Chinese Chemical Society. (2019)
Suggested Citation
Cheng Yuan Liu, Taveechai Wititsuwannakul, Chu Han Hsieh, Chung Yu Tsai, Ting Hsuan Wang, Ram Ambre, Wen Ching Chen, Panida Surawatanawong, Tiow Gan Ong Nickel-mediated cross-coupling via C–O activation assisted by organoaluminum. Journal of the Chinese Chemical Society. (2019). doi:10.1002/jccs.201900450 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/50595
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Nickel-mediated cross-coupling via C–O activation assisted by organoaluminum
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.