ArticleChemical science2022
Photochemical synthesis of 1,2,4-triazoles
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Fundamental Study of Density Functional Theory Applied to Triplet State Reactivity: Introduction of the TRIP50 Data Set.Journal of chemical theory and computation · 2026Article
- Photolytic Access to Oxaspirodecanes and Chromenes from Vinyldiazo Ester Cycloaddition withJournal of the American Chemical Society · 2025Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Unveiling catalyst-free electro-photochemical reactivity of aryl diazoesters and facile synthesis of oxazoles, imide-fused pyrroles and tetrahydro-epoxy-pyridinesChemical science · 2023Article
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Authors and funding
7 authors.
Funding
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Abstract
The reactivity of diazoalkanes most commonly proceeds through the formation of carbene intermediates or dipolar cycloaddition reactions. The reaction of diazoalkanes with intermediates with unpaired electrons, however, is much less elaborated. Herein, we report on the photochemical reaction of acceptor-only diazoalkanes with azodicarboxylates. Photoexcitation of the latter results in the formation of a triplet species, which undergoes an addition reaction with diazoalkanes and formation of an azomethine ylide followed by dipolar cycloaddition reaction with organic nitriles to give a 1,2,4-triazole. The application of this transformation was elaborated in a broad and general substrate scope (48 examples), including scale-up
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