Base-mediated carboxylation of unprotected indole derivatives with carbon dioxide

Woo-Jin Yoo; Montse Guiteras Capdevila; Xiangwei Du; Shū Kobayashi

doi:10.1021/ol3025082

Base-mediated carboxylation of unprotected indole derivatives with carbon dioxide

Org Lett. 2012 Oct 19;14(20):5326-9. doi: 10.1021/ol3025082. Epub 2012 Oct 4.

Authors

Woo-Jin Yoo¹, Montse Guiteras Capdevila, Xiangwei Du, Shū Kobayashi

Affiliation

¹ Department of Chemistry, School of Science, The University of Tokyo, 7-3-1, Hongo, Tokyo, 113-0033, Japan.

PMID: 23035967
DOI: 10.1021/ol3025082

Abstract

A simple and straightforward method for the preparation of indole-3-carboxylic acids was discovered through the direct carboxylation of indoles with atmospheric pressure of carbon dioxide (CO(2)) under basic conditions. The key for the reaction was found to be the use of a large excess of LiO(t)Bu as a base to suppress the undesired decarboxylation side reaction.