at Google ScholarTitle data
Li, Fang ; Pei, Chao ; Koenigs, Rene M.:
Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds : a combined experimental and mechanistic study.
In: Chemical Science.
Vol. 12
(2021)
.
- pp. 6362-6369.
ISSN 2041-6539
DOI: https://doi.org/10.1039/D1SC00495F
Abstract in another language
Herein, we report on our studies on the reaction of organoselenium compounds with triazoles under thermal conditions using simple Rh(II) catalysts. These reactions do not provide the product of classic rearrangement reactions. Instead two different cascade reactions were uncovered. While allyl selenides react in a cascade of sigmatropic rearrangement and selenium-mediated radical cyclization reaction to give dihydropyrroles, cinnamyl selenides undergo a double rearrangement reaction cascade involving a final aza-Cope reaction to give the product of 1,3-difunctionalization. Theoretical and experimental studies were conducted to provide an understanding of the reaction mechanism of these cascade reactions. The former provide an important insight into fundamental question on the nature of the ylide intermediate in rearrangement reactions and reveal that organoselenium compounds take up multiple roles in rearrangement reactions and mediate a free ylide reaction mechanism.
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 Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry II - Bioorganic Chemistry |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 01 Apr 2025 11:13 |
| Last Modified: | 14 May 2025 07:54 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93110 |