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    Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination

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    Type
    Article
    Authors
    Liu, Xiangqian
    Hsiao, Chien-Chi
    Kalvet, Indrek
    Leiendecker, Matthias
    Guo, Lin
    Schoenebeck, Franziska
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-04-08
    Online Publication Date
    2016-04-08
    Print Publication Date
    2016-05-10
    Permanent link to this record
    http://hdl.handle.net/10754/623142
    
    Metadata
    Show full item record
    Abstract
    In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C-O bond-cleaving alkylation, for the first time without the limiting β-hydride elimination. This new nickel-catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process.
    Citation
    Liu X, Hsiao C-C, Kalvet I, Leiendecker M, Guo L, et al. (2016) Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination. Angewandte Chemie International Edition 55: 6093–6098. Available: http://dx.doi.org/10.1002/anie.201510497.
    Sponsors
    X.L. and L.G. were supported by the China Scholarship Council, C.-C.H. was supported by a DAAD fellowship, and M.L. was supported by a Kekule fellowship (Fonds der Chemischen Industrie) and the Studienstiftung des deutschen Volkes. We gratefully acknowledge the computing time granted on the RWTH Bull Cluster in Aachen (JARA0091).
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/anie.201510497
    10.1002/ange.201510497
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201510497
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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