Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans

• DOI: 10.3762/bjoc.7.146
• Publication Date: 2011-09-12T16:44:39Z
• Authors: Verónica Guilarte; M Pilar Castroviejo; Estela Álvarez; Roberto Sanz
• Keywords: o-zincation; Organic; Science; Q; selectivity; Chemistry, Organic; Organic chemistry; Química orgánica; palladium; 01 natural sciences; Full Research Paper; 0104 chemical sciences; Chemistry; benzo[b]furans; QD241-441

A new route to regioselectively dialkoxy-functionalized benzo[b]furan derivatives has been developed from 3-halo-2-iodoanisoles bearing an additional methoxy group, which have been accessed through an ortho-zincation/iodination reaction. Two palladium-catalyzed processes, namely a Sonogashira coupling followed by a tandem hydroxylation/cyclization sequence, give rise to new and interesting dimethoxy-substituted benzo[b]furans.