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

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Presentation transcript:

2. Metalation of  -Deficient Heteroaromatics

Metalation of  - Deficient Heteroaromatics. Bare Pyridines. Acidity Considerations Metalation of  - Deficient Heteroaromatics. Bare Pyridines. Acidity Considerations

Nu - Addition to Pyridines. Synthetic Utility

Directed ortho Metalation (DoM) Reactivity of Pyridines

C-based Pyridine DoM. DMG = CONEt 2 Synthetic Application C-based Pyridine DoM. DMG = CONEt 2 Synthetic Application

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

C-Based Methoxypyridine DoM. DMG = CH(O - )NR 2

HetAtom - Based Pyridine DoM. DMG = OCONR 2 HetAtom - Based Pyridine DoM. DMG = OCONR 2

HetAtom - Based Pyridine DoM. DMG = OCONR 2. Methodology HetAtom - Based Pyridine DoM. DMG = OCONR 2. Methodology

HetAtom - Based Pyridine DoM. DMG = OCONR 2. Anionic ortho-Fries Rearrangement HetAtom - Based Pyridine DoM. DMG = OCONR 2. Anionic ortho-Fries Rearrangement

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

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

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

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

HetAtom-Based Pyridine DoM. DMG = SO 2 NR 2, SO 2 N - R Methodology and Application HetAtom-Based Pyridine DoM. DMG = SO 2 NR 2, SO 2 N - R Methodology and Application

HetAtom-Based Quinoline DoM. DMG = OCONEt 2 Methodology HetAtom-Based Quinoline DoM. DMG = OCONEt 2 Methodology

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

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

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

Diazine DoM. Application to Nucleosides Diazine DoMDoM. Application to Nucleosides

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

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

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

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