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

Organic & Biomolecular Chemistry Pub Date: 2013-02-21 DOI: 10.1039/C3OB27477B

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
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