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gem-Selective Cross-Dimerization and Cross-Trimerization of Alkynes with Silylacetylenes Promoted by a Rhodium–Pyridine–N-Heterocyclic Carbene Catalyst

Authors

  • Ramón Azpíroz,

    1. Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)
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  • Dr. Laura Rubio-Pérez,

    1. Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)
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  • Dr. Ricardo Castarlenas,

    Corresponding author
    1. Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)
    2. ARAID Foundation Researcher
    • Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)

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  • Prof. Jesús J. Pérez-Torrente,

    1. Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)
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  • Prof. Luis A. Oro

    Corresponding author
    1. Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)
    2. Center of Research Excellence in Refining & Petrochemicals, King Fahd University of Petroleum & Minerals, Dhahran 31261 (Saudi Arabia)
    • Departamento de Química Inorgánica-ISQCH, Universidad de Zaragoza - CSIC, Facultad de Ciencias, C/Pedro Cerbuna 12, 50009 Zaragoza (Spain)

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Abstract

The gem-selective cross-dimerization and -trimerization of silylacetylenes with alkynes through C[BOND]H activation using a rhodium(I)–pyridine–N-heterocyclic carbene catalyst have been developed. This reaction is applied to various aliphatic or aromatic terminal alkynes, internal alkynes, and gem-1,3-disubsituted enynes to afford the corresponding enynes and dienynes with high regio- and stereoselectivities and in good isolated yields (up to 91 %).

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