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Synlett 1993; 1993(4): 269-270
DOI: 10.1055/s-1993-22663
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A Facile One-Pot Synthesis of Polyfunctionalized 2-Unsubstituted Benzo[b]furans

Ilaria Candiani* , Silvia DeBernardinis, Walter Cabri, Marcello Marchi, Angelo Bedeschi, Sergio Penco
  • *Farmitalia Carlo Erba, R&D, via Giovanni XXIII, 23, I-20014 Nerviano (MI), Italy
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Publication Date:
19 March 2002 (online)

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A facile one-pot synthesis of 2-unsubstituted highly functionalized benzo[b]furans is reported. The synthesis includes the coupling of an iodophenol derivative with (trimethylsilyl)acetylene, catalyzed by a Pd(0)/Cu(I) system, and a regioselective cyclizationdeprotection step mediated by TMG (1,1,3,3-tetramethylguanidine) and SiO2. Selective reductions then afford the dihydro analogues.