Synthesis of maleic anhydrides and maleic acids by Pd-catalyzed oxidative dicarbonylation of alk-1-ynes

被引:50
作者
Gabriele, B [1 ]
Veltri, L
Salerno, G
Costa, M
Chiusoli, GP
机构
[1] Univ Calabria, Dipartimento Sci Farmaceut, I-87036 Arcavacata Di Rende, Cosenza, Italy
[2] Univ Calabria, Dipartimento Chim, I-87036 Arcavacata Di Rende, Cosenza, Italy
[3] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
关键词
anhydrides; carbonylation; maleic acids; palladium;
D O I
10.1002/ejoc.200200706
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 60-80degreesC in the presence of catalytic amounts of PdI2 in conjunction with KI and under a 4.1.10 mixture of CO/air/CO2, 160 atm total pressure at 25degreesC. 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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码:1722 / 1728
页数:7
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