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Empel, Claire ; Jana, Sripati ; Koodan, Adithyaraj ; Koenigs, Rene M.:
Unlocking C–H Functionalization at Room Temperature via a Light-Mediated Protodemetalation Reaction.
In: ACS Catalysis.
Bd. 12
(2022)
.
- S. 8229-8236.
ISSN 2155-5435
DOI: https://doi.org/10.1021/acscatal.2c01267
Abstract
Herein, we report on the photocatalytic ortho-alkylation reaction of 2-phenyl pyridines with N-protected maleimides using [Cp*RhCl2]2 as a catalyst and propionic acid as an additive at room temperature. Experimental and theoretical studies suggest a reaction mechanism that consists of a dark and a light reaction: while cyclometalation and migratory insertion can proceed at room temperature in the dark, the photochemical excitation of reaction intermediates is required to facilitate the decomplexation of the directing group and allow a ligand exchange with propionic acid. This photochemical ligand exchange enables a facile protodemetalation reaction to regenerate the catalyst and give the reaction product. We studied this reaction in a broad substrate scope, including different directing groups and N-substituted maleimides to yield succinimides in high yield (49 examples, up to 96% yield).
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Keywords: | photocatalysis; rhodium; C−H functionalization; alkylation reaction; DFT calculations |
| 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: | 31 Mär 2025 11:40 |
| Letzte Änderung: | 31 Mär 2025 11:40 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93076 |