4.8 Article

Copper-Mediated Trifluoromethylation-Allylation of Arynes

Journal

ORGANIC LETTERS
Volume 20, Issue 4, Pages 1179-1182

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00101

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Funding

  1. Research Grants Council of Hong Kong [CUHK 24301217]
  2. Chinese University of Hong Kong (the Faculty Strategic Fund for Research from the Faculty of Science)
  3. Chinese University of Hong Kong (Direct Grant for Research) [4053199]

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An unprecedented three-component copper-mediated vicinal trifluoromethylation-allylation of arynes is described. A wide range of structurally diverse trifluoromethylated allylarenes can be quickly assembled in one step. The application of the method has been demonstrated in the expedient synthesis of the CF3-containing analogue of the antispasmodic drug papaverine. The new reactivity of the [CuCF3] reagent, which is generated from the inexpensive industrial byproduct fluoroform, is revealed with unique advantages.

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