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Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-03-25 , DOI: 10.1002/chem.201905812 Amanda F da Silva 1 , Marco A S Afonso 1 , Rodrigo A Cormanich 1 , Igor D Jurberg 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-03-25 , DOI: 10.1002/chem.201905812 Amanda F da Silva 1 , Marco A S Afonso 1 , Rodrigo A Cormanich 1 , Igor D Jurberg 1
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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.
中文翻译：
蓝光辐照增强了芳基重氮乙酸酯与硼酸的室温偶联。
据报道可见光促进的光化学方案用于芳基重氮乙酸酯与硼酸的偶联。与没有光照的相同方案相比，这种光化学反应显示出极大的增强。除少数情况外，在黑暗（热过程）中的室温耦合通常不起作用。如果这样做的话，很可能还涉及到游离卡宾作为关键中间体。可替代地，光化学反应显示出广泛的范围，可以在空气中进行并且耐受各种各样的官能团。反应进化监测，DFT计算和控制实验已用于评估这种复杂机制的主要方面。具有生物活性的分子阿迪芬，苯那西嗪和阿普生已经被制备为合成应用的实例。
更新日期：2020-04-22
中文翻译：
蓝光辐照增强了芳基重氮乙酸酯与硼酸的室温偶联。
据报道可见光促进的光化学方案用于芳基重氮乙酸酯与硼酸的偶联。与没有光照的相同方案相比，这种光化学反应显示出极大的增强。除少数情况外，在黑暗（热过程）中的室温耦合通常不起作用。如果这样做的话，很可能还涉及到游离卡宾作为关键中间体。可替代地，光化学反应显示出广泛的范围，可以在空气中进行并且耐受各种各样的官能团。反应进化监测，DFT计算和控制实验已用于评估这种复杂机制的主要方面。具有生物活性的分子阿迪芬，苯那西嗪和阿普生已经被制备为合成应用的实例。
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