Trisannelation of acrylates to 1,3,5-benzenetricarboxylates by a Pd(OAc)2/HPMoV/CeCl3/O2 system.
Trisannelation of acrylates to 1,3,5-benzenetricarboxylates by a Pd(OAc)2/HPMoV/CeCl3/O2 system.
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DOI：
10.1021/jo070323e
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发表时间：
2007-04
期刊：
影响因子：
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通讯作者：
Ken-ichi Tamaso;Y. Hatamoto;S. Sakaguchi;Y. Obora;Y. Ishii
中科院分区：
文献类型：
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作者：
Ken-ichi Tamaso;Y. Hatamoto;S. Sakaguchi;Y. Obora;Y. Ishii
在常压二氧条件下，Pd(OAc)2与钼钒过磷酸（HPMo8V4）和Lewis酸结合，形成缩醛生成丙烯酸酯的新型三烷基化反应。因此，在O2 （1atm）和MeOH/AcOH中，Pd(OAc)2、HPMo8V4和CeCl3存在下，丙烯酸异丁酯在O2 （1atm）下反应得到了产率相当的1,3,5-苯三羧酸异丁酯。发现该反应是通过钯催化丙烯酸酯与甲醇的缩醛化，然后由CeCl3促进缩醛的三烷基化反应进行的。
A new type of trisannelation reaction of acrylates through acetal formation was developed by Pd(OAc)2 combined with molybdovanadophosphoric acid (HPMo8V4) and Lewis acid under atmospheric dioxygen. Thus, the reaction of isobutyl acrylate in the presence of Pd(OAc)2, HPMo8V4, and CeCl3 under O2 (1 atm) in MeOH/AcOH afforded isobutyl 1,3,5-benzenetricarboxylate in fair yield. The reaction was found to proceed through the palladium-catalyzed acetalization of acrylate with methanol followed by the trisannelation reaction of the resulting acetal promoted by CeCl3.