Direct Arylation of Benzo[ b]furan and Other Benzo-Fused Heterocycles

European J Org Chem. 2014 Dec;2014(36):8119-8125. doi: 10.1002/ejoc.201403125. Epub 2014 Nov 17.

Abstract

The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]furan.

Keywords: Arylation; Concerted metal deprotonation; C–H activation; Fused-ring systems; Palladium; Regioselectivity; Synthetic methods.