Electrochemical α-Arylation of Ketones via Anodic Oxidation of In Situ Generated Silyl Enol Ethers.
J Org Chem
; 86(22): 16026-16034, 2021 11 19.
Article
en En
| MEDLINE
| ID: mdl-34343004
ABSTRACT
An electrochemical procedure for the α-arylation of ketones has been developed. The method is based on the generation and one-pot anodic oxidation of silyl enol ethers in the presence of the arene. This strategy avoids isolation of the silyl enol intermediate and the utilization of external supporting electrolytes. Intermolecular arylations, which had not been reported so far, are possible when electron-rich arenes are utilized as coupling partners. The method has been demonstrated for a wide variety of aryl ketones and activated arenes, with moderate to good yields (up to 69%) obtained. Mechanistic insights and a theoretical rationale that explains the ketone α-arylation versus dimerization selectivity are also presented.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Éteres
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Cetonas
Idioma:
En
Revista:
J Org Chem
Año:
2021
Tipo del documento:
Article
País de afiliación:
Austria