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Synfacts 2013; 9(1): 0083
DOI: 10.1055/s-0032-1317734
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide

Contributor(s):
Paul Knochel
,
Christoph Sämann
Yoo W.-J, Capdevila MG, Du X, Kobayashi S * The University of Tokyo, Japan
Base Mediated Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide.

Org. Lett. 2012;
14: 5326-5329
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

carboxylation - indoles - carbon dioxide - lithium

Significance

A practical and straight-forward method for the preparation of indole-3-carboxylic acids has been reported. Deprotonation with LiOt-Bu under an atmospheric pressure of carbon dioxide furnishes a variety of indole-3-carboxylic acids in high yield.


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Comment

The described reaction is very versatile since it tolerates various functional groups and has therefore a broad substrate scope. According to the authors, the large excess of LiOt-Bu suppresses the undesired decarboxylation side reaction.


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