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

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 coupli...

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Veröffentlicht in:Beilstein journal of organic chemistry 2011-09, Vol.7 (1), p.1255-1260
Hauptverfasser: Guilarte, Verónica, Castroviejo, M Pilar, Alvarez, Estela, Sanz, Roberto
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Sprache:eng
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Zusammenfassung: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.146