A Domino Approach of Heck Coupling for the Synthesis of β-Trifluoromethylstyrenes

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Abstract

A domino approach of Heck coupling was used to synthesize β-trifluoromethylstyrene derivatives from iodoarenes and 1-iodo-3,3,3-trifluoropropane in moderate to good yields. This method avoids the use of low-boiling, gaseous reagents such as 3,3,3-trifluoropropene, and additives and phosphines in the catalytic system.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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  Electrophilic Trifluoromethylation by Copper-Catalyzed Addition of CF₃-Transfer Reagents to Alkenes and Alkynes

  Pär G. Janson, Ibrahim Ghoneim, Nadia O. Ilchenko, and Kálmán J. Szabó
  Organic Letters2012 Article ASAP

  • Electrophilic Trifluoromethylation by Copper-Catalyzed Addition of CF₃-Transfer Reagents to Alkenes and Alkynes

    Pär G. Janson, Ibrahim Ghoneim, Nadia O. Ilchenko, and Kálmán J. Szabó
    Organic Letters2012 Article ASAP

    Regio- and stereoselective Cu-catalyzed addition of the above hypervalent iodine reagent to alkynes and alkenes was achieved. In the presence of CuI, the reaction is suitable to perform trifluoromethyl-benzoyloxylation and trifluoromethyl-halogenation of ...

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• 

  Simple Synthesis of β-Trifluoromethylstyrenes Using (E)-Trimethyl-(3,3,3-trifluoroprop-1-enyl)silane

  Masaaki Omote, Miyuu Tanaka, Akari Ikeda, Shiho Nomura, Atsushi Tarui, Kazuyuki Sato, and Akira Ando
  Organic Letters2012 14 (9), 2286-2289

  • Simple Synthesis of β-Trifluoromethylstyrenes Using (E)-Trimethyl-(3,3,3-trifluoroprop-1-enyl)silane

    Masaaki Omote, Miyuu Tanaka, Akari Ikeda, Shiho Nomura, Atsushi Tarui, Kazuyuki Sato, and Akira Ando
    Organic Letters2012 14 (9), 2286-2289

    (E)-Trimethyl-(3,3,3-trifluoroprop-1-enyl)silane (1) was synthesized as a reagent for use in Hiyama cross-coupling reactions for the production of β-trifluoromethylstyrene derivatives. Cross-coupling of 1 with electronically diverse aryl iodides was ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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