Department of Organic Chemistry, Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-862, Campinas, SP, Brazil.
Chemistry. 2020 May 4;26(25):5648-5653. doi: 10.1002/chem.201905812. Epub 2020 Mar 25.
A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
可见光促进的光化学反应协议被报道用于芳基重氮乙酸酯与硼酸的偶联。与没有光照时进行的相同协议相比，这种光化学反应有很大的增强。除了少数情况外，在黑暗中（热过程）室温偶联通常不起作用。当它起作用时，它也可能涉及自由碳烯作为关键中间体。或者，光化学反应具有广泛的范围，可以在空气中进行，并能耐受各种官能团。反应演化监测、DFT 计算和控制实验已被用于评估这一复杂的机制情景的主要方面。生物活性分子 adiphenine、benactyzine 和 aprophen 已被制备为合成应用的例子。
