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Reactivity of Stabilized Vinyl Diazo Derivatives toward Unsaturated Hydrocarbons: Regioselective Gold-Catalyzed Carbon–Carbon Bond Formation

Authors

  • Prof. José Barluenga,

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
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  • Giacomo Lonzi,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
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  • Prof. Miguel Tomás,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
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  • Dr. Luis A. López

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33007-Oviedo (Spain), Fax: (+34) 989-510-3450
    Search for more papers by this author

Abstract

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They struck gold! New reaction modes were observed in the gold-catalyzed reaction of alkenyldiazo compounds and unsaturated substrates. The process represents a new C[BOND]C bond-formation reaction in which alkenes, alkynes, and arenes are active reagents for the Cγ-allylation, -allenylation, and -arylation, respectively, of alkenyldiazo substrates (see scheme). The reactivity pattern is likely to rely on the formation of a highly electrophilic alkenylgold carbenoid, which may be involved in a carbocation-type mechanism.

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