2. Metalation of p-Deficient Heteroaromatics - PowerPoint PPT Presentation

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2. Metalation of p-Deficient Heteroaromatics

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C-based Pyridine DoM. DMG = CON-R. HetRing Annelation. C-Based Methoxypyridine DoM. ... HetAtom-Based Pyridine DoM. DMG = SO2NR2, SO2N-R. Methodology and Application ... – PowerPoint PPT presentation

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Title: 2. Metalation of p-Deficient Heteroaromatics


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."
25
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