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The light “on-off” stepwise one-pot method for 3,4-diaryl coumarins with potential AIE properties
Tetrahedron ( IF 2.1 ) Pub Date : 2020-10-18 , DOI: 10.1016/j.tet.2020.131677
Huijuan Zhang , Qingrui Li , Yunnian Yin , Jung Keun Kim , Mengmeng Huang , Yabo Li , Yangjie Wu

An efficient one-pot method involving visible-light-induced cyclization and Pd-catalyzed Suzuki cross-coupling processes to construct 3,4-diaryl coumarins is developed. Under the light on-off optimized conditions, a series of alkynoates and aryl boronic acids were well suitable for this catalytic system, and were successfully transformed into the corresponding products in moderate to high yields. Meanwhile, this synthetic system has good applicability for other Pd-catalyzed coupling reactions, such as Heck and Sonogashira reactions. 3,4,7-Triphenyl coumarin could be produced not only via the Suzuki reaction of 3-bromo-4,7-diphenyl with PhB(OH)2, but also via the Pd-catalyzed C–H activation. Based on the spectral studies, we found that some of the 3,4-diaryl coumarins may have AIE activities. This work provides a straight forward way to create valuable multi-substituted coumarins with potential AIE properties.



中文翻译:

具有潜在AIE性能的3,4-二芳基香豆素的轻型“开关”逐步一锅法

开发了一种有效的一锅法,该方法涉及可见光诱导的环化和Pd催化的Suzuki交叉偶联过程,以构建3,4-二芳基香豆素。在开-关优化条件下,一系列炔酸和芳基硼酸非常适合该催化体系,并已成功地以中等至高收率转化为相应的产物。同时,该合成体系对于其他Pd催化的偶联反应如Heck和Sonogashira反应具有良好的适用性。3,4,7-三苯基香豆素不仅可以通过3-bromo-4,7-diphenyl与PhB(OH)2的Suzuki反应生成,而且可以通过Pd催化的CH活化。根据光谱研究,我们发现某些3,4-二芳基香豆素可能具有AIE活性。这项工作提供了一种直接的方法来创建具有潜在AIE特性的有价值的多取代香豆素。

更新日期:2020-11-21
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