Wosińska-Hrydczuk Marzena, Yaghoobi Anzabi Mohadese, Przeździecki Jakub, Danylyuk Oksana, Chaładaj Wojciech, Gryko Dorota
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
ACS Org Inorg Au. 2024 Jun 12;4(4):418-423. doi: 10.1021/acsorginorgau.4c00019. eCollection 2024 Aug 7.
Under light irradiation, aryldiazo acetates can generate either singlet or triplet carbenes depending on the reaction conditions, but heteroaryl diazo compounds have remained underexplored in this context. Herein, we found that triazolyl diazoacetates exhibit higher reactivity than their aryl counterparts. They even react with dichloromethane (DCM), a common, inert solvent, for photoreactions involving diazo reagents, giving halogenated products. Theoretical studies show that all reactions involve carbenes but progress via different pathways depending on the solvent used.
在光照射下，芳基重氮乙酸酯可根据反应条件生成单线态或三线态卡宾，但在这种情况下，杂芳基重氮化合物的研究仍较少。在此，我们发现三唑基重氮乙酸酯比其芳基类似物表现出更高的反应活性。它们甚至能与二氯甲烷（DCM）（一种常见的惰性溶剂）发生反应，用于涉及重氮试剂的光化学反应，生成卤代产物。理论研究表明，所有反应都涉及卡宾，但根据所用溶剂的不同，反应通过不同的途径进行。
