Double coupling reactions of 3,4-bis(stannyl)furanone: facile preparation of diaryl- and dibenzylfuranones

Carter, N.B., Mabon, R., Walmsley, R., Richecoeur, A.M.E. and Sweeney, J.B. (2006) Double coupling reactions of 3,4-bis(stannyl)furanone: facile preparation of diaryl- and dibenzylfuranones. Synlett, 2006 (11). pp. 1747-1749. ISSN 0936-5214 doi: 10.1055/s-2006-944209

Abstract/Summary

The palladium-catalyzed cross-coupling reaction of 3,4-bis(tributylstannyl)furan-2(5H)-one using chelating ligand or polar solvent gives mixtures of single and double coupled products, even when one equivalent of halide coupling partner is used. After optimization, the double coupling reaction was shown to be general, with the use of two equivalents of aryl iodides giving 3,4-disubstituted furanones, The reaction using benzyl bromides proceeds at lower temperatures than the corresponding coupling using aryl iodides, giving dibenzylfuranones. The methodology has been exemplified in a synthesis of (+/-)-hinokinin.