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Metalation of p-Deficient Heteroaromatics: Synthesis and Applications

Explore the reactivity of C-based heteroaromatic compounds in metalation reactions, focusing on ortho metalation and directed ortho metalation, with emphasis on synthetic applications and methodology development.

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Metalation of p-Deficient Heteroaromatics: Synthesis and Applications

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  1. 2. Metalation of p-Deficient Heteroaromatics

  2. Metalation of p- Deficient Heteroaromatics. Bare Pyridines. Acidity Considerations

  3. Nu- Addition to Pyridines. Synthetic Utility

  4. Directed ortho Metalation (DoM) Reactivity of Pyridines

  5. C-based Pyridine DoM. DMG = CONEt2 Synthetic Application

  6. C-based Pyridine DoM. DMG = CON-R HetRing Annelation

  7. C-Based Methoxypyridine DoM. DMG = CH(O-)NR2

  8. HetAtom - Based Pyridine DoM. DMG = OCONR2

  9. HetAtom - Based Pyridine DoM. DMG = OCONR2. Methodology

  10. HetAtom - Based Pyridine DoM. DMG = OCONR2. Anionic ortho-Fries Rearrangement

  11. HetAtom - Based Pyridine DoM. DMG = N-COt-Bu. Synthetic Application

  12. HetAtom-Based Pyridine DoM. DMG = F, Cl. “Catalytic” Metalation. 3-Formyl-2-halopyridines

  13. HetAtom-Based Pyridine DoM. DMG = F, Cl. Methodological Results

  14. HetAtom-Based Pyridine DoM. DMG = I, F. Tandem DoM / Halogen Dance Reactions of Iodopyridines

  15. HetAtom-Based Pyridine DoM. DMG = SO2NR2, SO2N-R Methodology and Application

  16. HetAtom-Based Quinoline DoM. DMG = OCONEt2 Methodology

  17. HetAtom - Based Quinoline DoM. DMG = N-COt-Bu. Methodology

  18. Diazine DoM. Pyrimidines, DMG = OMe. Methodology

  19. Diazine DoM. Pyrimidines, DMG = Cl. Methodology and Synthetic Utility

  20. Diazine DoM . Application to Nucleosides Diazine DoM . Application to Nucleosides

  21. Diazine DoM. Pyridazines, DMG = Cl. Methodology

  22. Diazine DoM. Pyridazines, DMG = Cl. Addition of s- and n-BuLi

  23. Diazine DoM. Pyrazines, DMG = CON-t-Bu, N-COt-Bu Unusual Reactivity

  24. "I thought you said it was spot to spot."

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