Metal‐Mediated Formation of Carbon–Halogen Bonds

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Abstract
Organic halides represent basic starting materials for numerous metal-catalyzed organic transformations. Generally, the carbon–halogen is broken in the first step, that is, an oxidative addition reaction, of the catalytic cycle. On the other hand, very little is known about the reverse reaction, carbon–halogen reductive elimination from a transition-metal center. In this Concept article, we describe the examples of C(sp3)halide and C(sp2)halide reductive-elimination reactions which demonstrate that this type of reactivity can be quite common in organometallic chemistry. Although the thermodynamic driving force for the formation of carbon–halogen bonds is relatively small, the kinetic barrier for these reactions can also be low. Thus, Chalide reductive elimination can compete favorably with the more established organic transformations, such as CC reductive elimination.