Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base

[Image: see text] Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is pres...

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Detalles Bibliográficos
Autores principales: Lee, Seulchan, Kim, Si Ae, Jang, Hye-Young
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822219/
https://www.ncbi.nlm.nih.gov/pubmed/31681903
http://dx.doi.org/10.1021/acsomega.9b03064
Descripción
Sumario:[Image: see text] Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is presumed to play an important role in the cleavage of the C–H bond at the benzylic position of peroxide intermediates, which were formed by the reaction with oxygen.

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