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Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications

Literature Meeting March 25, 2008. Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications. David Marcoux Charette’s Laboratories. Importance (Natural Products). Importance (Drugs). Importance (Drugs). Importance (Materials).

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Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications

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  1. Literature Meeting March 25, 2008 Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications David Marcoux Charette’s Laboratories

  2. Importance (Natural Products)

  3. Importance (Drugs)

  4. Importance (Drugs)

  5. Importance (Materials)

  6. Common C(aryl)-N Bond Formation (Reductive Amination and Alkylation)

  7. Common C(aryl)-N Bond Formation (SNAr)

  8. Common C(aryl)-N Bond Formation (Nitration)

  9. Common C(aryl)-N Bond Formation (Ullman Reaction)

  10. Common C(aryl)-N Bond Formation(Larock Indole Synthesis)

  11. Common C(aryl)-N Bond Formation (Aryne Chemistry)

  12. Common C(aryl)-N Bond Formation (Pd-Mediated)

  13. Hartwig-Buchwald Pd-Catalyzed C(Aryl)-X Coupling

  14. Pd-Catalyzed C-C Coupling

  15. Catalytic Cycle

  16. Generation of the Active Catalyst

  17. Oxidative Addition

  18. Transmetallation

  19. Isomerisation

  20. Reductive Elimination

  21. b-H Elimination

  22. Migita First Results in Pd-Catalyzed C(Aryl)-N Bond Formation

  23. Prof. John F. Hartwig

  24. Hartwig First Look

  25. Hartwig First Look

  26. Catalytic Cycle with Tin Amide

  27. Prof. Stephen L. Buchwald

  28. Buchwald First Look

  29. First Coupling Using Free Amine

  30. First Coupling Using Free Amine

  31. Intramolecular Version

  32. Side Product

  33. Real Problem

  34. 2 Weeks Later

  35. Hartwig’s Conditions

  36. Unsolved Problems

  37. BINAP Scope

  38. Back-to-Back

  39. Mechanism

  40. Why ArI are Less Reactive

  41. Etheral Solvents

  42. Lower Temperature

  43. Why 18-C-6 ?

  44. Pyridine Containing Substrates

  45. Chiral Amine

  46. Bidentate Ligand

  47. Mechanism

  48. Scope

  49. Limitation

  50. Ligand Screening

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