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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
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Published on: May 21, 2019
Copper-Mediated Late-Stage Radical Trifluoromethylation of Pyrazole-Type Scaffolds
Lucie S Eisen1,2, Jan H Griwatz2, Sven Ruf2
1Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country, Manuel Lardizabal 3, 20080 San Sebastián, Spain.
None:
Trifluoromethylated pyrazoles and their derivatives are of great interest due to their biological and pharmacological relevance. However, efficient methods for their preparation via late-stage trifluoromethylation strategies remain limited. Herein, we report a practical and efficient method for the direct trifluoromethylation of pyrazoles using in situ generated CF3 radicals and inexpensive copper-(II) salts as catalysts at room temperature. The method exhibits excellent functional group tolerance. DFT studies support the observed reactivity trends and provide insight into the electronic effects governing CF3 radical addition. This strategy holds promise for the generation of highly substituted pyrazoles of interest in biomedical and crop-science applications.
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