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Double Coupling Reactions of 3,4-Bis(stannyl)furanone: Facile Preparation of Diaryl- and Dibenzylfuranones

Sweeney, Joseph B., Carter, Neil, Mabon, Ross, Walmsley, Rachel and Richecœur, Alexandre (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

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Abstract

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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Joseph Sweeney
Date Deposited: 18 Oct 2012 12:19
Last Modified: 18 Oct 2012 12:19
URI: http://eprints.hud.ac.uk/id/eprint/15223

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