Transition-Metal-Mediated and -Catalyzed C-F Bond Activation by Fluorine Elimination

The activation of carbon-fluorine (C-F) bonds is an important topic in synthetic organic chemistry. Metal-mediated and -catalyzed elimination of beta- or alpha-fluorine proceeds under milder conditions than oxidative addition to C-F bonds. The beta- or alpha-fluorine elimination is initiated from organometallic intermediates having fluorine substituents on carbon atoms beta or alpha 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.