at Google ScholarTitle data
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.
Vol. 12
(2022)
.
- pp. 8229-8236.
ISSN 2155-5435
DOI: https://doi.org/10.1021/acscatal.2c01267
Abstract in another language
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).
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | photocatalysis; rhodium; C−H functionalization; alkylation reaction; DFT calculations |
| 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: | 31 Mar 2025 11:40 |
| Last Modified: | 07 Oct 2025 08:27 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93076 |