Carbazoaniline: Enantioselektive Kreuz-dehydrogenative Aminierungsreaktionen für die Darstellung asymmetrischer chiraler Diamine und ihre Anwendung als enantiomerenreinen Liganden
Zusammenfassung der Projektergebnisse
In conclusion, the project was in large part devoted to the exploration of the redox reactivity of phenothiazines (PTZs) and derivatives, in particular in metal-free cross dehydrogenative coupling reactions with phenols and indoles. Indeed, a notable serendipitous discovery at the beginning of project, led us to explore this reactivity. Although we deviated considerably from our original project objectives, we are nevertheless now closer to reaching the main objective than before (enantioselective C-N bond forming coupling reactions with H-bonded axial chirality). Indeed, many of the herein coupling methods operate now at more moderate temperatures, some at only 40 °C, and the vast majority of the new C-N coupled products are C-N chiral in the case of unsymmetrically substituted phenothiazine starting materials. Indeed, in most cases, a strong intramolecular O-H•••N Hydrogen-bond is evidenced by IR and X-ray. These objectives remain therefore on our list of realistic future goals.
Projektbezogene Publikationen (Auswahl)
- O2-mediated dehydrogenative amination of phenols. Angew. Chem. Int. Ed. 2015, 54, 4102
M.-L. Louillat-Habermeyer, R. Jin & F. W. Patureau
(Siehe online unter https://doi.org/10.1002/anie.201500089) - Mild, periodate mediated, dehydrogenative C-N bond formation with phenothiazines and phenols, Org. Lett. 2016, 18, 4491
R. Jin, F. W. Patureau
(Siehe online unter https://doi.org/10.1021/acs.orglett.6b02223) - The cumene/O2 system: a very simple tool for the radical chain oxidation of some functional groups. N. J. Chem. 2017, 41, 6981
A. Malekafzali, K. Malinovska, F. W. Patureau
(Siehe online unter https://doi.org/10.1039/c7nj01666b) - Mechanism of the Dehydrogenative Phenothiazination of Phenols. Chem. Eur. J. 2018, 24
M. Goswami, A. Konkel, M. Rahimi, M.-L. Louillat-Habermeyer, H. Kelm, R. Jin, B. de Bruin, F. W. Patureau
(Siehe online unter https://doi.org/10.1002/chem.201800730) - Phenothiazinimides: atom-efficient electrophilic amination reagents. Org. Lett., 2018, 20, 2884
R. Jin, C. L. Bub, F. W. Patureau
(Siehe online unter https://doi.org/10.1021/acs.orglett.8b00914) - The strong Beta-CF3 shielding effect in HFIP and 100 other organic solvents revisited with O NMR. ChemCatChem 2018, 10, 1547
A. Bernhardt, H. Kelm, F. W. Patureau
(Siehe online unter https://doi.org/10.1002/cctc.201701721)
