Issue 37, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
27 ม.ค. 2560
Accepted
11 เม.ย. 2560
First published
12 เม.ย. 2560

Chem. Commun., 2017,53, 5117-5120

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

V. Lanke and K. R. Prabhu, Chem. Commun., 2017, 53, 5117 DOI: 10.1039/C7CC00763A

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