A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed. The perfluoroalkylated cyanoalkenes that are produced can be readily transformed into useful fluoroalkylated derivatives.
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| http://dx.doi.org/10.1021/acs.orglett.9b02648 | DOI Listing |
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Copper(I)-Catalyzed Cyanoperfluoroalkylation of Alkynes.
Org Lett
September 2019
State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People's Republic of China.
A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed.
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