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.

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。