Transcript 11_Lecture - Ventura College

Organic Chemistry
6th Edition
Paula Yurkanis Bruice
Chapter 11
Organometallic
Compounds
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Organometallic Compounds
An organic compound containing a carbon–metal bond
Organolithium compounds and organomagnesium
compounds are two of the most common organometallic
compounds
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Preparation of Organolithium
Compounds
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Preparation of Organomagnesium
Compounds
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Alkyl halides, vinyl halides, and aryl halides can all be
used to form organolithium and organomagnesium
compounds
However, these organometallic compounds cannot be
prepared from compounds containing acidic groups
(OH, NH2, NHR, SH, C=CH, CO2H)
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Coupling Reactions
Preparation of the Gilman reagent:
Example of carbon–carbon formation using the
Gilman reaction:
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Gilman reagents can be used to prepare compounds
that cannot be prepared by using nucleophilic
substitution reactions:
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Gilman reagents can replace halogens in compounds
containing other functional groups:
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The Heck Reaction
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The Stille Reaction
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The Suzuki Coupling
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Mechanism of the Suzuki
Coupling Reaction
Oxidative addition: Pd (0) to Pd (II):
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Hydroxide exchange:
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Transmetallation:
Reductive elimination:
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Mechanism of the Heck
Coupling Reaction
Oxidative addition: Pd (0) to Pd (II):
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 Complex formation:
 complex
Insertion:
 complex
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Elimination:
Trans
stereochemistry
Regeneration of the catalyst:
Undergoes oxidative
addition to bromobenzene
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