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)
    Search for more papers by this author
  • 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)
    Search for more papers by this author
  • 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)
    Search for more papers by this author
  • 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)
    Search for more papers by this author

  • 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

The combo pack: Copper-catalyzed trifluoromethylation of alkenes bearing an allylic proton combined with C[BOND]C bond formation affords the title compounds in good to high yields (see scheme). The reactions are faster than allylic trifluoromethylation, especially in 1,4-dioxane. A unique 1,6-oxytrifluoromethylation occurred instead of an anticipated seven-membered ring forming carbotrifluoromethylation reaction.

Ancillary