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    Selectivity switch in the synthesis of vinylgold(I) intermediates

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    Type
    Article
    Authors
    Hashmi, A. Stephen K
    Schuster, Andreas M.
    Gaillard, Sylvain
    Cavallo, Luigi cc
    Poater, Albert cc
    Nolan, Steven P. cc
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2011-11-28
    Permanent link to this record
    http://hdl.handle.net/10754/561930
    
    Metadata
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    Abstract
    An unexpected regioselectivity reversal was observed in the synthesis of vinylgold(I) complexes from propargyl carboxamides. The use of [Au(IPr)(OH)] affords preferentially vinylgold(I) complexes resulting from a 5-exo-dig cyclization, whereas the use [Au(IPr)]+ species, generated in situ starting from [Au(IPr)(Cl)] and AgOTf, leads to vinylgold(I) complexes which form via a 6-endo-dig cyclization, This unexpected "selectivity switch" for this cyclization led us to propose two different reaction pathways enabling the formation of the two different products. One mechanism involves the [Au(IPr)]+ species with "classical" I activation of the alkyne framework of the carboxamides, and the second represents an "unusual" use of the basic Brønsted character of [Au(IPr)(OH)]. Mechanistic and DFT studies support the mechanistic hypotheses. © 2011 American Chemical Society.
    Citation
    Hashmi, A. S. K., Schuster, A. M., Gaillard, S., Cavallo, L., Poater, A., & Nolan, S. P. (2011). Selectivity Switch in the Synthesis of Vinylgold(I) Intermediates. Organometallics, 30(22), 6328–6337. doi:10.1021/om2009556
    Sponsors
    The ERC (FUNCAT to SPN) and the EPSRC are gratefully acknowledged for support of this work. A.P. thanks the Spanish MICINN for a Ramon y Cajal contract (RYC-2009-04170). Umicore AG and Chemetall AG are thanked for their generous gifts of materials. S.P.N. is a Royal Society Wolfson Research Merit Award holder. We thank Dr. Pierrick Nun for valuable discussions.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organometallics
    DOI
    10.1021/om2009556
    ae974a485f413a2113503eed53cd6c53
    10.1021/om2009556
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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