Selective synthesis of ( Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5 H)-furanones

4-Aryl-3-bromo-2(5 H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5 H)-furanone either with arylboronic acids in the presence of Ag 2O and a catalytic amount of PdCl 2(MeCN) 2 or with aryl(trialkyl)stannanes in the presence of a c...

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Bibliographic Details
Published in:Tetrahedron 2001-12, Vol.57 (50), p.9997-10007
Main Authors: Bellina, Fabio, Anselmi, Chiara, Viel, Stéphane, Mannina, Luisa, Rossi, Renzo
Format: Article
Language:English
Subjects:
biologically active compounds
boron and compounds
coupling reactions
furanones
tin and compounds
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Summary:4-Aryl-3-bromo-2(5 H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5 H)-furanone either with arylboronic acids in the presence of Ag 2O and a catalytic amount of PdCl 2(MeCN) 2 or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh 3 and a Pd(II) or a Pd(0) compound. These monobromo derivatives have been then used as precursors to a variety of ( Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5 H)-furanones including the compound with the structure corresponding to that reported for naturally occurring rubrolide N. The structure and stereochemistry of these synthetic compounds have been unambiguously established by NMR techniques. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)01017-1