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Decarbonylative Borylation of Amides by Palladium Catalysis

[Image: see text] The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides...

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Detalles Bibliográficos
Autores principales: Shi, Shicheng, Szostak, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647946/
https://www.ncbi.nlm.nih.gov/pubmed/31459674
http://dx.doi.org/10.1021/acsomega.9b00081
Descripción
Sumario:[Image: see text] The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides by highly selective carbon–nitrogen bond cleavage by palladium catalysis. The approach capitalizes on the ground-state destabilization of the amide bond in N-acyl glutarimides to achieve Pd-catalyzed insertion into the amide N–C bond and decarbonylation (deamidation). Mechanistic studies and the utility of this methodology in orthogonal sequential cross-couplings of robust, bench-stable amides are reported.