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Copper‐Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes
Author(s) -
Li Xiaohong,
Fu Bin,
Zhang Qiao,
Yuan Xiuping,
Zhang Qian,
Xiong Tao,
Zhang Qian
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010492
Subject(s) - regioselectivity , nucleophile , chemistry , catalysis , reagent , silanes , organic chemistry , combinatorial chemistry , compatibility (geochemistry) , materials science , silane , composite material
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.