Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2005, Issue 12, Pages 2481-2490Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200400856
Keywords
fused-ring systems; heterogeneous catalysis; oxidative coupling; oxygen heterocycles; palladium
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The synthesis of a series of 2,3-diarylbenzo[b]furans starting from 1,2-diarylethanones and 1,2-dibromoarenes proceeds by means of both homogeneous and polymer-anchored palladium catalysts. This tandem process can be effectively halted at the C-arylation step, thus providing key o-bromoarylated deoxybenzoin intermediates in good yields. The efficient oxidative coupling leading to benzo[b]phenanthro[9,10-d]furans is carried out using the safer hypervalent iodine reagent PIFA. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
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