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Copper‐Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes

Xiaohong Li, Bin Fu, Qiao Zhang, Xiuping Yuan, Qian Zhang, Tao Xiong, Qian Zhang

2020Angewandte Chemie International Edition52 citationsDOI

Abstract

A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism.

Topics & Concepts

RegioselectivityChemistryNucleophileCatalysisSilanesReagentCombinatorial chemistryOrganic chemistrySilaneFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis
Copper‐Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes | Litcius