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Iridium(III) catalyzed regioselective amidation of indoles at the C4-position using weak coordinating groups

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Abstract

The C4-aminated indole scaffold is frequently encountered in several natural products and biologically active compounds. Herein we disclose a simple and short synthetic route for the amidation of indoles at the C4 position by employing an aldehyde as a directing group and Ir(III) as a catalyst. This strategy offers high selectivity for the C4-amidation of unprotected and protected indoles. A simple deprotection of the tosyl group leads to the formation of C4-amino indole derivatives, which are useful synthons for synthesizing natural products in the teleocidin family.

Graphical abstract: Iridium(iii) catalyzed regioselective amidation of indoles at the C4-position using weak coordinating groups

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Publication details

The article was received on 27 Jan 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC00763A
Citation: Chem. Commun., 2017, Advance Article
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    Iridium(III) catalyzed regioselective amidation of indoles at the C4-position using weak coordinating groups

    V. Lanke and K. R. Prabhu, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC00763A

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