A new regioselective synthesis of 3-substituted furan-2(5 H)-ones by palladium-catalysed reductive carbonylation of alk-1-ynes

3-Alkyl- or 3-aryl-substituted furan-2(5 H)-ones are obtained directly in fair yields by reductive carbonylation of alk-1-ynes in the presence of catalytic amounts of palladium iodide in conjunction with potassium iodide (10 eq.) and water (200 eq.). Simultaneous oxidation of CO to CO 2 accounts for...

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Bibliographic Details
Published in:Tetrahedron letters 1999-01, Vol.40 (5), p.989-990
Main Authors: Gabriele, Bartolo, Salerno, Giuseppe, Costa, Mirco, Chiusoli, Gian Paolo
Format: Article
Language:English
Subjects:
alkynes
carbonylation
furanones
palladium
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Summary:3-Alkyl- or 3-aryl-substituted furan-2(5 H)-ones are obtained directly in fair yields by reductive carbonylation of alk-1-ynes in the presence of catalytic amounts of palladium iodide in conjunction with potassium iodide (10 eq.) and water (200 eq.). Simultaneous oxidation of CO to CO 2 accounts for the stoichiometry of the process. Reactions are carried out in dioxane under mild conditions (80 °C and 10 atm of carbon monoxide). Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02464-2