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CHAPTER 11
Organometallic Compounds
Important Terms
alkene metathesis
(olefin metathesis)
a reaction that breaks the double bond of an alkene and then rejoins the
fragments to form a new double bond between two
sp
2
carbons that were not
previously bonded.
alkyne metathesis
a reaction that breaks the triple bond of an alkyne and then rejoins the fragments to
form a new triple bond between two
sp
carbons that were not previously bonded.
coupling reaction
dialkyl lithium cuprate
Gilman reagent
(organocuprate)
Grignard reagent
(organomagnesium compound)
organocuprate
(Gilman reagent)
organomagnesium compound
(Grignard reagent)
organolithium compound
organometallic compound
a reaction that joins two groups with a carbon–carbon bond.
(R)
2
CuLi; prepared by treating an organolithium reagent with cuprous iodide.
a dialkyl lithium cuprate used to replace a halogen in an alkyl, aryl, or vinylic
halide with an alkyl group.
RMgBr or RMgCl; prepared by adding an alkyl halide to magnesium shavings.
olefin metathesis
(alkene metathesis)
a reaction that breaks the double bond of an alkene and then rejoins the fragments to
form a new double bond between two
sp
2
carbons that were not previously bonded.
a dialkyl lithium cuprate used to replace a halogen in an alkyl, aryl, or vinylic
halide with an alkyl group.
Heck reaction
a reaction that couples an aryl halide or a vinylic halide with an alkene.
organoboron compound
an alkyl-organoboron compound, an alkenyl-organoboron compound, or an
aryl-organoboron compound: R B(OR)
2
.
RLi; prepared by adding lithium to an alkyl halide.
a compound with a carbon–metal bond.
organopalladium compound
a compound with a palladium–carbon bond.
oxidative addition
reductive elimination
Suzuki reaction
insertion of a metal between two atoms.
elimination of a metal from between two carbons, resulting in formation of a
carbon–carbon bond.
a reaction that couples an aryl halide or vinylic halide with an organoboron reagent.
transmetallation
the exchange of two groups (often alkyl and halide) between two metals.
RMgBr or RMgCl; prepared by adding an alkyl halide to magnesium shavings.