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Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon–Carbon Bond in 2-Aryl-1-tetralones

[Image: see text] Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonst...

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Detalles Bibliográficos
Autor principal: Ghosh, Partha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648412/
https://www.ncbi.nlm.nih.gov/pubmed/31459896
http://dx.doi.org/10.1021/acsomega.9b00732
Descripción
Sumario:[Image: see text] Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol helps in understanding the mechanism of the reaction.