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合成了一个新的化合物4-溴-5-碘间二苯甲酸8,用于在交叉偶联反应中一系列的化学选择性测试.基于交叉偶联反应中的功能基团反应活性原理,4-溴-5-碘间二苯甲酸分别同1-癸炔进行Sonogashira交叉偶联反应以及同苯硼酸进行Suzuki交叉偶联反应,反应后所得到的产物证明反应仅发生在反应活性更高的部位,而较5-碘基活性稍小的4-溴基被保留仍可进行另一次的交叉偶联反应.这种类型的溴化物11虽然受到5位碘的空间位阻效应以及1,3-位吸电子基团的影响仍然显示了很高的化学活性.因此根据此方法,4-溴-5-碘间二苯甲酸参与反应时不用采取对功能基团的保护或转化,可作为很好的直接进行分步交叉偶联反应的基础原料,这将大大简化和缩短合成其它长共轭的芳香烃化合物的路线.
A new compound, 4-bromo-5-iodo-m-dibenzoic acid 8, was synthesized for a series of chemoselectivity tests in cross-coupling reactions. Based on the functional group reactivity theory in cross-coupling reaction, -bromo-5-iodo-dibenzoic acid with Sonogashira cross-coupling reaction with 1-decyne and Suzuki cross-coupling reaction with phenylboronic acid respectively. The product obtained after the reaction proves that the reaction only takes place in the sites with higher reactivity , While 4-bromo, which is slightly less active than 5-iodo, is retained for another cross-coupling reaction This type of bromide 11, though sterically hindered by the 5-position iodine, According to this method, 4-bromo-5-iodo-m-dibenzoic acid does not need to take protection or conversion of the functional groups in the reaction and can be regarded as very good Of the direct step-by-step cross-coupling reaction of the basic raw materials, which will greatly simplify and shorten the synthesis of other long conjugated aromatic hydrocarbon routes.