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

作者：Macdonald Jonathan; Oldfield Victoria; Bavetsias Vassilios; Blagg Julian^*

来源：Organic and Biomolecular Chemistry, 2013, 11(14): 2335-2347.

DOI：10.1039/c3ob27477b

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.

• 出版日期2013