4.5 Article

Nucleophilic Trifluoromethylthiolation of Allylic Bromides: A Facile Preparation of Allylic Trifluoromethyl Thioethers

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 31, Issue 7, Pages 921-926

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201300415

Keywords

trifluoromethylthiolation; allylic halides; copper

Funding

  1. National Natural Science Foundation of China [21072030]
  2. Research Fund for the Doctoral Program of Higher Education of China [20123514110003]
  3. Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012-1707]
  4. Fuzhou University [022318, 022494]

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A facile preparation of allylic trifluoromethyl thioethers was achieved by using a copper reagent. The reaction of (bpy)Cu(SCF3) with various allylic bromides afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Common functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated.

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