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    Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst

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    Type
    Article
    Authors
    El-Sepelgy, Osama
    Brzozowska, Aleksandra
    Sklyaruk, Jan
    Jang, Yoon Kyung
    Zubar, Viktoriia
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2018-01-18
    Online Publication Date
    2018-01-18
    Print Publication Date
    2018-02-02
    Permanent link to this record
    http://hdl.handle.net/10754/626891
    
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    Abstract
    A new iron-catalyzed chemoselective intramolecular hydroamination and hydroalkoxylation of the readily available α-allenic amines and alcohols to valuable unsaturated 5-membered heterocycles, 2,3-dihydropyrrole and 2,3-dihydrofuran, is reported. Effective selectivity control is achieved by a metal–ligand cooperative activation of the substrates. The mild reaction conditions and the use of low amounts of an air and moisture stable iron catalyst allow for the hydrofunctionalization of a wide range of allenes bearing different functional groups in good yields in the absence of base or any sensitive additives.
    Citation
    El-Sepelgy O, Brzozowska A, Sklyaruk J, Jang YK, Zubar V, et al. (2018) Cooperative Metal–Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst. Organic Letters. Available: http://dx.doi.org/10.1021/acs.orglett.7b03828.
    Sponsors
    J.S. thanks FCI for the predoctoral fellowship.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/acs.orglett.7b03828
    Additional Links
    http://pubs.acs.org/doi/10.1021/acs.orglett.7b03828
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.orglett.7b03828
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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