Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

Koji Nemoto, Satoru Onozawa, Naoki Egusa, Naoya Morohashi, Tetsutaro Hattori

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.

Original languageEnglish
Pages (from-to)4512-4514
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number31
DOIs
Publication statusPublished - 2009 Aug 5

Keywords

  • Alumination
  • Carboxylation
  • Indolecarboxylic acid
  • Pyrrolecarboxylic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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