A carbometallation is any reaction where a carbon-metal bond reacts with a carbon-carbon π-bond to produce a new carbon-carbon σ-bond and a carbon-metal σ-bond.[1] The resulting carbon-metal bond can undergo further carbometallation reactions (oligomerization or polymerization see Ziegler-Natta polymerization) or it can be reacted with a variety of electrophiles including halogenating reagents, carbonyls, oxygen, and inorganic salts to produce different organometallic reagents. Carbometallations can be performed on alkynes and alkenes to form products with high geometric purity or enantioselectivity, respectively. Some metals prefer to give the anti-addition product with high selectivity and some yield the syn-addition product. The outcome of syn and anti- addition products is determined by the mechanism of the carbometallation.
^Negishi, Ei-ichi; Tan, Ze (2005), "Diastereoselective, Enantioselective, and Regioselective Carboalumination Reactions Catalyzed by Zirconocene Derivatives", Metallocenes in Regio- and Stereoselective Synthesis: -/-, Topics in Organometallic Chemistry, Springer Berlin Heidelberg, pp. 139–176, doi:10.1007/b96003, ISBN 9783540314523
(1997-02-01). "Anti-Carbometalation of Homopropargyl Alcohols and Their Higher Homologues via Non-Chelation-Controlled Syn-Carbometalation and Chelation-Controlled...
a respiratory irritant. Industrial production is through catalytic carbometalation: toluene adds to propene in the presence of a sodium-potassium catalyst...
beta-hydride elimination. The reaction is structurally related to carbometalation. When the substrate is an alkyne the reaction product is a vinylorganometallic...
β-hydride elimination electron transfer carbon-hydrogen bond activation carbometalation hydrometalation cyclometalation nucleophilic abstraction The synthesis...
gives the trans-alkene. For the preparation multisubstituted alkenes, carbometalation of alkynes can give rise to a large variety of alkene derivatives....
in an alkenylcopper compound (R2C=C(R)−Cu). It is a special case of carbometalation and also called the Normant reaction. The Chan-Lam coupling enables...
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