0000000000447235
AUTHOR
Kevin D. Moeller
Electrochemical synthesis of benzoxazoles from anilides - a new approach to employ amidyl radical intermediates.
A novel electrochemical method for the synthesis of benzoxazoles from readily available anilides is reported. Various functionalities are tolerated and good yields can be achieved. By employing common electrode materials and a simple constant current protocol, this method is an attractive new alternative to conventional pathways.
Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling
The electrochemical synthesis of pyrazolidine-3,5-diones and benzoxazoles by N-N bond formation and C,O linkage, respectively, represents an easy access to medicinally relevant structures. Electrochemistry as a key technology ensures a safe and sustainable approach. We gained insights in the mechanism of these reactions by combining cyclovoltammetric and synthetic studies. The electron-transfer behavior of anilides and dianilides was studied and led to the following conclusion: The N-N bond formation involves a diradical as intermediate, whereas the benzoxazole formation is based on a cationic mechanism. Besides these studies, we developed a synthetic route to mixed dianilides as starting m…
CCDC 1561793: Experimental Crystal Structure Determination
Related Article: Tile Gieshoff, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, Siegfried R. Waldvogel|2017|J.Am.Chem.Soc.|139|12317|doi:10.1021/jacs.7b07488
CCDC 1561794: Experimental Crystal Structure Determination
Related Article: Tile Gieshoff, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, Siegfried R. Waldvogel|2017|J.Am.Chem.Soc.|139|12317|doi:10.1021/jacs.7b07488
CCDC 1561792: Experimental Crystal Structure Determination
Related Article: Tile Gieshoff, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, Siegfried R. Waldvogel|2017|J.Am.Chem.Soc.|139|12317|doi:10.1021/jacs.7b07488
CCDC 1530094: Experimental Crystal Structure Determination
Related Article: Tile Gieshoff, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, Siegfried R. Waldvogel|2017|Chem.Commun.|53|2974|doi:10.1039/C7CC00927E