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Published on: July 17, 2020
Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions
Marzena Wosińska-Hrydczuk1, Mohadese Yaghoobi Anzabi1, Jakub Przeździecki1,2
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Abstract:
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.
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