Synthesis of Maleic Anhydrides and Maleic Acids by Pd-Catalyzed Oxidative Dicarbonylation of Alk-1-ynes

We have found that carbon dioxide effectively promotes the Pd‐catalyzed oxidative carbonylation of terminal alkynes to give maleic anhydrides in fair yields. Reactions were carried out in aqueous dioxane at 60−80 °C in the presence of catalytic amounts of PdI2 in conjunction with KI and under a 4:1:...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-05, Vol.2003 (9), p.1722-1728
Main Authors: Gabriele, Bartolo, Veltri, Lucia, Salerno, Giuseppe, Costa, Mirco, Chiusoli, Gian Paolo
Format: Article
Language:English
Subjects:
Anhydrides
Carbonylation
Maleic acids
Palladium
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Summary:We have found that carbon dioxide effectively promotes the Pd‐catalyzed oxidative carbonylation of terminal alkynes to give maleic anhydrides in fair yields. Reactions were carried out in aqueous dioxane at 60−80 °C in the presence of catalytic amounts of PdI2 in conjunction with KI and under a 4:1:10 mixture of CO/air/CO2 (60 atm total pressure at 25 °C). By working in the presence of a large excess of water, maleic acids were formed selectively with unprecedented catalytic efficiencies for this kind of reaction. In the latter case, the use of an excess of carbon dioxide tended to inhibit, rather than promote, the reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200210706