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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)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Light-Induced PdH-Catalyzed Cross-Dimerization of gem-Difluoroalkenes with Alkenes to Access CF2H Motifs
Luning Shen1, Fen Wu2, Dachang Bai2
1Pingyuan Laboratory, State Key Laboratory of Antiviral Drugs, School of Chemistry and Chemical Engineering, School of Pharmaceutical Sciences, Henan Normal University, Xinxiang 453007, China.
Abstract:
The CF2H group constitutes a valuable structural motif in medicinal chemistry. Herein, we report an efficient light-induced palladium-catalyzed cross-dimerization of electron-deficient gem-difluoroalkenes with styrene derivatives, enabling hydroalkenylation and hydroalkylation reactions to access diverse α-difluoromethyl products. The photoenhanced hydricity of PdH species facilitates efficient insertion into gem-difluoroalkenes for the generation of α-difluoromethyl palladium species. This palladium intermediate subsequently undergoes alkyl Heck reaction with readily available alkenes without defluorination, affording C(sp3)-C(sp2) coupling products with monosubstituted alkenes, or C(sp3)-C(sp3) coupling products with 1,1-disubstituted alkenes. This protocol features mild conditions and broad functional group tolerance.
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