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![[(DPEPhos)(bcp)Cu]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)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
General Method for Selective C(sp2)-H Trifluoromethylation of Enamides via Visible Light Dual Photoredox/Nickel
Zhe Qi1, Xian-Hua Pan1, Li-Fang Wang1
1Faculty of Flavour Fragrance and Cosmetics, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai201418, P. R. China.
Abstract:
Fluoroalkylated enamides are pivotal intermediates and drug-forming scaffolds in organic synthesis. Herein, we report a visible-light-promoted photoredox/nickel protocol for the (E)-β-trifluoromethylation of N-vinyl secondary enamides using sodium trifluoromethanesulfinate. This newly developed protocol allows for facile and divergent access to various stereodefined β-CF3 in high yields and excellent stereoselectivity from readily available starting materials. We also report a one-step synthesis of the pyrimidine derivative trifluorothymine, the purine nucleoside analogue 5-(trifluoromethyl)uridine, and the antiviral drug trifluridine to demonstrate synthetic utility. Mechanistic investigations, including radical-trapping experiments and control experiments, reveal the radical nature of the reaction.
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