Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation

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Abstract

Demonstrating direct synergic ''low polarity metallation'', 1-methylindole is C-magnesiated by (TMEDA)2?Na2MgBu4 and C-zincated by (TMEDA)?Na(tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised.
LanguageEnglish
Pages2864-2866
Number of pages2
JournalChemical Communications (London)
Issue number27
DOIs
Publication statusPublished - 2007

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Alkali Metals
Aromatic compounds
Thymidine Monophosphate
Metals
phenyllithium
N-methylpyrrole
1-methylindole

Keywords

  • aromatic compounds
  • low polarity metallation

Cite this

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title = "Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation",
abstract = "Demonstrating direct synergic ''low polarity metallation'', 1-methylindole is C-magnesiated by (TMEDA)2?Na2MgBu4 and C-zincated by (TMEDA)?Na(tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised.",
keywords = "aromatic compounds, low polarity metallation",
author = "R.E. Mulvey and A.R. Kennedy and E. Hevia",
year = "2007",
doi = "10.1039/b704362g",
language = "English",
pages = "2864--2866",
journal = "Chemical Communications (London)",
issn = "0009-241X",
number = "27",

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AU - Mulvey, R.E.

AU - Kennedy, A.R.

AU - Hevia, E.

PY - 2007

Y1 - 2007

N2 - Demonstrating direct synergic ''low polarity metallation'', 1-methylindole is C-magnesiated by (TMEDA)2?Na2MgBu4 and C-zincated by (TMEDA)?Na(tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised.

AB - Demonstrating direct synergic ''low polarity metallation'', 1-methylindole is C-magnesiated by (TMEDA)2?Na2MgBu4 and C-zincated by (TMEDA)?Na(tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised.

KW - aromatic compounds

KW - low polarity metallation

UR - http:/dx.doi.org/10.1039/b704362g

U2 - 10.1039/b704362g

DO - 10.1039/b704362g

M3 - Article

SP - 2864

EP - 2866

JO - Chemical Communications (London)

T2 - Chemical Communications (London)

JF - Chemical Communications (London)

SN - 0009-241X

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ER -