Copper-Catalyzed Nucleophilic Trifluoromethylation of Allylic Halides: A Simple Approach to Allylic Trifluoromethylation

Authors

  • Dr. Yoshihiro Miyake,

    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan), Fax: (+81) 3-5841-1175
    Search for more papers by this author
  • Shin-ichi Ota,

    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan), Fax: (+81) 3-5841-1175
    Search for more papers by this author
  • Prof. Dr. Yoshiaki Nishibayashi

    Corresponding author
    1. Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan), Fax: (+81) 3-5841-1175
    • Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656 (Japan), Fax: (+81) 3-5841-1175
    Search for more papers by this author

Abstract

original image

Trifluoromethylation: The treatment of allylic halides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(I) thiophene-2-carboxylate (CuTC) gives the corresponding allylic trifluoromethylation products in good to high yields and with complete regioselectivity (see scheme). The use of THF as a solvent is crucial for obtaining good yields of product.

Ancillary