Hoeeg, Finn and Luxenberger, Lea and Fedulin, Andrey and von Wangelin, Axel Jacobi (2024) Cobalt-catalyzed double hydroboration of pyridines. CHEMICAL SCIENCE, 15 (14). pp. 5201-5210. ISSN 2041-6520, 2041-6539
Full text not available from this repository. (Request a copy)Abstract
Cobalt(ii) complexes were prepared from a modular phosphinopyridonate platform and applied to the hydroboration of pyridines. The synthetically useful, yet challenging, double hydroboration toward tetrahydropyridine derivatives was successfully performed with high activity and regiocontrol. This new method enabled the direct synthesis of N-heterocyclic allylic boronates from commercial pyridines and pinacolborane (HBpin). One-pot acetylation afforded the bench-stable borylated N-acetyl tetrahydropyridines in good yields. The synthetic utility of this procedure was demonstrated by a gram-scale double hydroboration-acetylation sequence followed by chemical diversification. Mechanistic experiments indicated metal-ligand cooperativity involving ligand-centered C-H activation and the intermediacy of a cobalt(iii) hydride species. Cobalt phosphinopyridonates enabled the synthetically useful, yet challenging, double hydroboration of pyridines. Mechanistic studies indicated metal-ligand cooperativity, ligand-centered C-H activation and the intermediacy of a cobalt(iii) hydride.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | REGIOSELECTIVE 1,4-HYDROBORATION; BORYLATION; REDUCTION; COMPLEXES; SUBSTITUTION; HETEROCYCLES; ASTERISK; HYDRIDE; LIGANDS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Oct 2025 09:03 |
| Last Modified: | 14 Oct 2025 09:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/64725 |
Actions (login required)
 |
View Item |
