at Google ScholarTitle data
Cai, Bao-Gui ; Bao, Ye-Peng ; Pei, Chao ; Li, Qian ; Li, Lei ; Koenigs, Rene M. ; Xuan, Jun:
Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates.
In: Chemical Science.
Vol. 13
(2022)
.
- pp. 13141-13146.
ISSN 2041-6539
DOI: https://doi.org/10.1039/D2SC04720A
Abstract in another language
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 via flow chemistry and downstream transformations. Experimental and computational studies were performed to elucidate the reaction mechanism and to rationalize the reaction outcome.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry II - Bioorganic Chemistry > Chair Organic Chemistry II - Bioorganic Chemistry - Univ.-Prof. Dr. René M. Koenigs |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 31 Mar 2025 11:48 |
| Last Modified: | 14 May 2025 07:54 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93079 |