Journal
TETRAHEDRON LETTERS
Volume 50, Issue 31, Pages 4512-4514Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.05.076
Keywords
Carboxylation; Alumination; Indolecarboxylic acid; Pyrrolecarboxylic acid
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
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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. (C) 2009 Elsevier Ltd. All rights reserved.
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