Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition

Sarah Abou-Shehada, Matthew C. Teasdale, Steven D. Bull, Charles E. Wade, Jonathan M J Williams

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc-based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization. Pyridine gets active: For the first time, the catalytic activation of the pyridine ring towards nucleophilic aromatic substitution, conjugate addition, and Diels-Alder reactions is reported. The method utilizes a cheap, non-toxic zinc-based Lewis acid, which binds to the nitrogen of the pyridine ring and activates it towards nucleophilic aromatic substitution. The reaction tolerates a variety of incoming groups and proceeds cleanly and under mild reaction conditions.

Original languageEnglish
Pages (from-to)1083-1087
JournalChemSusChem
Volume8
Issue number6
Early online date13 Feb 2015
DOIs
Publication statusPublished - Mar 2015

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acid activation
Pyridines
Lewis Acids
Pyridine
substitution
Substitution reactions
Chemical activation
Acids
zinc
acid
nitrogen
Zinc
Nitrogen
Cyclization
pyridine
method

Keywords

  • Amination
  • Conjugate addition
  • Lewis acid
  • Pyridine
  • SAr

Cite this

Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition. / Abou-Shehada, Sarah; Teasdale, Matthew C.; Bull, Steven D.; Wade, Charles E.; Williams, Jonathan M J.

In: ChemSusChem, Vol. 8, No. 6, 03.2015, p. 1083-1087.

Research output: Contribution to journalArticle

Abou-Shehada, Sarah ; Teasdale, Matthew C. ; Bull, Steven D. ; Wade, Charles E. ; Williams, Jonathan M J. / Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition. In: ChemSusChem. 2015 ; Vol. 8, No. 6. pp. 1083-1087.
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