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    Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers

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    Type
    Article
    Authors
    Guo, Lin
    Liu, Xiangqian
    Baumann, Christoph
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-11-07
    Online Publication Date
    2016-11-07
    Print Publication Date
    2016-12-05
    Permanent link to this record
    http://hdl.handle.net/10754/623165
    
    Metadata
    Show full item record
    Abstract
    A nickel-catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B-alkyl 9-BBN and trialkylborane reagents that involves the cleavage of stable C(sp2)−OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp2)−C(sp3) bonds that does not suffer from β-hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C−O bonds is presented to demonstrate the advantage of this method.
    Citation
    Guo L, Liu X, Baumann C, Rueping M (2016) Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers. Angewandte Chemie International Edition 55: 15415–15419. Available: http://dx.doi.org/10.1002/anie.201607646.
    Sponsors
    L.G. and X.L. were supported by the China Scholarship Council.
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/anie.201607646
    10.1002/ange.201607646
    Additional Links
    http://onlinelibrary.wiley.com/doi/10.1002/anie.201607646/full
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201607646
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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