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Metal‐Mediated Formation of Carbon–Halogen Bonds
Author(s) -
Vigalok Arkadi
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701738
Subject(s) - reductive elimination , halide , oxidative addition , halogen , chemistry , catalysis , carbon fibers , organometallic chemistry , reactivity (psychology) , halogen bond , transition metal , catalytic cycle , photochemistry , inorganic chemistry , combinatorial chemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , composite number , composite material , alkyl
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(sp 3 )halide and C(sp 2 )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, Chalide reductive elimination can compete favorably with the more established organic transformations, such as CC reductive elimination.