1. Organometallic Compounds
Organic Chemistry
6th Edition
Paula Yurkanis Bruice
Chapter 11
Organometallic Compounds

3. Organometallic Compounds
An organic compound containing a carbon–metal bond
Organolithium compounds and organomagnesium
compounds are two of the most common organometallic
compounds

4. Preparation of Organolithium Compounds

5. Preparation of Organomagnesium Compounds

7. 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)

8. Coupling Reactions Preparation of the Gilman reagent:
Example of carbon–carbon formation using the Gilman reaction:

9. Gilman reagents can be used to prepare compounds
that cannot be prepared by using nucleophilic
substitution reactions:

10. Gilman reagents can replace halogens in compounds
containing other functional groups:

11. The Heck Reaction

12. The Stille Reaction

13. The Suzuki Coupling

14. Mechanism of the Suzuki Coupling Reaction
Oxidative addition: Pd (0) to Pd (II):

15. Hydroxide exchange:

16. Transmetallation:
Reductive elimination:

17. Mechanism of the Heck Coupling Reaction
Oxidative addition: Pd (0) to Pd (II):

18.  Complex formation:
 complex
Insertion:
 complex

19. Undergoes oxidative addition to bromobenzene
Elimination:
Trans
stereochemistry
Regeneration of the catalyst:
Undergoes oxidative addition to bromobenzene