Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions

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Authors
Wosińska-Hrydczuk, Marzena
Yaghoobi Anzabi, Mohadese
Przeździecki, Jakub
Danylyuk, Oksana
Chaładaj, Wojciech ORCID logo 0000-0001-8143-3788
Gryko, Dorota ORCID logo 0000-0002-5197-4222
Date
2024
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Creative Commons Attribution 4.0 International License
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.
Description
Keywords
photochemistry  diazo compounds  radicals  carbenes  triazole
Citation
ACS Org. Inorg. Au 2024, 4, 418−423 ; https://pubs.acs.org/doi/full/10.1021/acsorginorgau.4c00019
URI
https://open.icm.edu.pl/handle/123456789/24834
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