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Alkene Trifluoromethylation Coupled with C[BOND]C Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles

Authors

  • Dr. Hiromichi Egami,

    1. Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    2. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Ryo Shimizu,

    1. Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    2. Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan)
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  • Shintaro Kawamura,

    1. Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    2. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Prof. Dr. Mikiko Sodeoka

    Corresponding author
    1. Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    2. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    3. Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan)
    • Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • This work was supported in part by a Grant-in-aid for Young Scientists (B) from the MEXT (No. 23750116) and by Project Funding for Basic Science from RIKEN.

Abstract

original image

Mit vereinten Kräften liefern die kupferkatalysierte Trifluormethylierung von Alkenen, die Protonen in Allylstellung tragen, und eine C-C-Kupplung die Titelverbindungen in guten Ausbeuten (siehe Schema). Die Reaktionen sind, speziell in 1,4-Dioxan, schneller als die allylische Trifluormethylierung. Eine 1,6-Oxytrifluormethylierung tritt an die Stelle der erwarteten Carbotrifluormethylierung unter Bildung eines Siebenrings.

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