Issue 14, 2013

Regioselective C2-arylation of imidazo[4,5-b]pyridines

Abstract

We show that N3-MEM-protected imidazo[4,5-b]pyridines undergo efficient C2-functionalisation via direct C–H arylation. Twenty-two substituted imidazo[4,5-b]pyridines are prepared and iterative, selective elaboration of functionalised imidazo[4,5-b]pyridines gives 2,7- and 2,6-disubstituted derivatives in good yields from common intermediates. Mechanistic observations are consistent with a concerted-metallation-deprotonation mechanism facilitated by coordination of copper(I)iodide to the imidazo[4,5-b]pyridine.

Graphical abstract: Regioselective C2-arylation of imidazo[4,5-b]pyridines

Supplementary files

Article information

Article type
Paper
Submitted
20 Dec 2012
Accepted
11 Feb 2013
First published
21 Feb 2013
This article is Open Access

Org. Biomol. Chem., 2013,11, 2335-2347

Regioselective C2-arylation of imidazo[4,5-b]pyridines

J. Macdonald, V. Oldfield, V. Bavetsias and J. Blagg, Org. Biomol. Chem., 2013, 11, 2335 DOI: 10.1039/C3OB27477B

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