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The Mizoroki-Heck reaction in mesoionic 1-butyl-3-methyltetrazolium-5-olate
Tetrahedron ( IF 2.1 ) Pub Date : 2021-09-14 , DOI: 10.1016/j.tet.2021.132450
Hideaki Kurabayashi 1 , Tsunehisa Hirashita 1 , Shuki Araki 1
Affiliation  

1-Butyl-3-methyltetrazolium-5-olate (1), a mesoionic compound, exists as a liquid at room temperature and can be used as a polar solvent for the Mizoroki-Heck reaction, wherein it has been proven to be a superior solvent to other solvents. The reaction of iodobenzene with ethyl acrylate in the presence of palladium acetate in mesoionic liquid 1 at 40 °C for 24 h gave ethyl cinnamate in 78% yield in the absence of ligands, while the use of other solvents, such as [bmim][BF4], [bmim][PF6], and DMF gave lower yields (43%, 37%, and 17%, respectively) under the same conditions. Heck-type coupling reactions of electron-deficient or electron-rich aryl iodides and bromobenzenes with olefins (15 examples, 7%–97%) were performed in 1. When a phosphine ligand was added to the reaction mixture, aryl bromides could be used, and the mesoionic liquid containing the catalysts could be reused at least five times.



中文翻译:

介离子 1-丁基-3-甲基四唑鎓-5-油酸盐中的 Mizoroki-Heck 反应

1-Butyl-3- methyltetrazolium -5-olate ( 1 ) 是一种介离子化合物,在室温下以液体形式存在,可用作 Mizoroki-Heck 反应的极性溶剂,其中已被证明是一种优越的溶剂到其他溶剂。碘苯与丙烯酸乙酯在乙酸钯存在下在介离子液体1 中 在 40°C 下反应 24 小时,在没有配体的情况下以 78% 的产率得到肉桂酸乙酯,而使用其他溶剂,如 [bmim][在相同条件下,BF 4 ]、[bmim][PF 6 ] 和 DMF 的产率较低(分别为 43%、37% 和 17%)。缺电子或富电子芳基碘化物和溴苯与烯烃的 Heck 型偶联反应(15 个实例,7%–97%)在1 . 当在反应混合物中加入膦配体时,可以使用芳基溴化物,含有催化剂的介离子液体至少可以重复使用五次。

更新日期:2021-10-22
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