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Gold(I)-Catalyzed Tandem C−H and C−C Activation (Cleavage)

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    Gold(I)-Catalyzed Tandem C−H and C−C Activation (Cleavage)
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    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China
    [email protected]; [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2010, 12, 1, 116–119
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    https://doi.org/10.1021/ol902593f
    Published December 3, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    (Cyclopropylidenecyclohexyl)benzene derivatives, a kind of methylenecyclopropane (MCP) containing a cyclohexyl group, can undergo an interesting tandem intramolecular C−H and C−C bond activation through dehydrogenated rearrangement in the presence of AuPPh3Cl/AgOTf by transferring three hydrogen atoms from cyclohexane to cyclopropane, affording the corresponding biaryl derivatives in moderate to good yields. The reaction mechanism has also been carefully investigated by deuterium labeling experiments and DFT calculations.

    Copyright © 2009 American Chemical Society

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    Detailed description of experimental procedures, full characterization of new compounds shown in Tables 1 and 2 and Schemes 1−3. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2010, 12, 1, 116–119
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol902593f
    Published December 3, 2009
    Copyright © 2009 American Chemical Society
    Request reuse permissions

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