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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Copper-Promoted Reductive Cross-Coupling for Cyanodifluoromethylation of (Hetero)aryl Iodides with BrCF2CN
Xin-Jun Yang1, Zheng Wang1, Qin-Yuan Ni1
1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Abstract:
The cyanodifluoromethyl group (-CF2CN) has emerged as a valuable fluorinated motif, with growing recognition for its potential applications in medicinal chemistry and materials science. However, its efficient incorporation into organic compounds remains a synthetic challenge. Herein, we report a copper-promoted reductive cross-coupling protocol for the cyanodifluoromethylation of (hetero)aryl iodides using bromodifluoroacetonitrile (BrCF2CN) as a cost-effective and readily available reagent. This method demonstrates broad substrate compatibility, delivering target products in moderate to good yields under mild and operationally simple conditions. Successful gram-scale synthesis and late-stage functionalization of complex molecules further highlight the utility of the protocol.
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