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Directed lithiation of unprotected pyridinecarboxylic acids

✍ Scribed by Florence Mongin; François Trécourt; Guy Quéguiner

Book ID
104261836
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
229 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The lithium salts of 2-, 3-and 4-pyridinecarboxylic acids undergo deprotonation at the position adjacent to the carboxylate group when treated with LTMP in THF at 0 °C, -50 °C and -25 °C, respectively. The lithiation conditions could be extended to chloronieotinic acids, and even to an activated benzoic acid.

📜 SIMILAR VOLUMES

Directed lithiation of unprotected quino
Directed lithiation of unprotected quinolinecarboxylic acids
✍ Anne-Sophie Rebstock; Florence Mongin; François Trécourt; Guy Quéguiner 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 58 KB

The lithium salts of quinoline-2-carboxylic acid and 4-methoxyquinoline-2-carboxylic acid undergo deprotonation at C3 when treated with LTMP in THF at -25 and 0°C, respectively. The lithium salts of quinoline-3-and -4-carboxylic acids are more prone to nucleophilic addition; nevertheless, they are d