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Facile Access to Fluoromethylated Arenes by Nickel‐Catalyzed Cross‐Coupling between Arylboronic Acids and Fluoromethyl Bromide
Author(s) -
An Lun,
Xiao YuLan,
Min QiaoQiao,
Zhang Xingang
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502882
Subject(s) - nickel , catalysis , bromide , chemistry , combinatorial chemistry , catalytic cycle , molecule , functional group , compatibility (geochemistry) , coupling reaction , organic chemistry , materials science , composite material , polymer
The nickel‐catalyzed fluoromethylation of arylboronic acids was achieved with the industrial raw material fluoromethyl bromide (CH 2 FBr) as the coupling partner. The reaction proceeded under mild reaction conditions with high efficiency; it features the use of a low‐cost nickel catalyst, synthetic simplicity, and excellent functional‐group compatibility, and provides facile access to fluoromethylated biologically relevant molecules. Preliminary mechanistic studies showed that a single‐electron‐transfer (SET) pathway is involved in the catalytic cycle.