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Jana, Sripati ; Li, Fang ; Empel, Claire ; Verspeek, Dennis ; Aseeva, Polina ; Koenigs, Rene M.:
Stoichiometric Photochemical Carbene Transfer by Bamford–Stevens Reaction.
In: Chemistry : a European Journal.
Bd. 26
(2020)
.
- S. 2586-2591.
ISSN 1521-3765
DOI: https://doi.org/10.1002/chem.201904994
Abstract
The photolysis of diazoalkanes is a timely strategy to conduct carbene-transfer reactions under mild and metal-free reaction conditions, and has developed as an important alternative to conventional metal-catalyzed carbene-transfer reactions. One of the major limitations lies within the rapidly occurring side reaction of the carbene intermediate with remaining diazoalkane molecules that result in the use of an excess of the reaction partner and thus impacts on the reaction efficiency. Herein, we describe a protocol that takes advantage of the in situ generation of donor–acceptor diazoalkanes by Bamford–Stevens reaction. Following this strategy, the concentration of the diazoalkane reaction partner can be minimized to reduce unwanted side reactions and to now conduct photochemical carbene transfer reactions under stoichiometric reaction conditions. We have explored this approach in the C−H and N−H functionalization and cyclopropanation reaction of N-heterocycles and could demonstrate the applicability of this method in 51 examples.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie |
| Titel an der UBT entstanden: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 02 Apr 2025 09:13 |
| Letzte Änderung: | 02 Apr 2025 09:13 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93146 |