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Transition‐Metal‐Mediated and ‐Catalyzed C−F Bond Activation by Fluorine Elimination
Author(s) -
Fujita Takeshi,
Fuchibe Kohei,
Ichikawa Junji
Publication year - 2019
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.201805292
Subject(s) - fluorine , chemistry , catalysis , bond cleavage , transition metal , heteroatom , reductive elimination , oxidative addition , carbon fibers , organometallic chemistry , elimination reaction , metal , photochemistry , combinatorial chemistry , organic chemistry , ring (chemistry) , materials science , composite number , composite material
The activation of carbon–fluorine (C−F) bonds is an important topic in synthetic organic chemistry. Metal‐mediated and ‐catalyzed elimination of β‐ or α‐fluorine proceeds under milder conditions than oxidative addition to C−F bonds. The β‐ or α‐fluorine elimination is initiated from organometallic intermediates having fluorine substituents on carbon atoms β or α to metal centers, respectively. Transformations through these elimination processes (C−F bond cleavage), which are typically preceded by carbon–carbon (or carbon–heteroatom) bond formation, have been increasingly developed in the past five years as C−F bond activation methods. In this Minireview, we summarize the applications of transition‐metal‐mediated and ‐catalyzed fluorine elimination to synthetic organic chemistry from a historical perspective with early studies and from a systematic perspective with recent studies.