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Chapter 11 Organometallic Compounds

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

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

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

  3. Preparation of Organolithium Compounds

  4. Preparation of Organomagnesium Compounds

  5. 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)

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

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

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

  9. The Heck Reaction

  10. The Stille Reaction

  11. The Suzuki Coupling

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

  13. Hydroxide exchange:

  14. Transmetallation: • Reductive elimination:

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

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

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

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