Cargando…

Synthesis of Benzylic Alcohols by C–H Oxidation

[Image: see text] Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(metha...

Descripción completa

Detalles Bibliográficos
Autores principales: Tanwar, Lalita, Börgel, Jonas, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6863597/
https://www.ncbi.nlm.nih.gov/pubmed/31689095
http://dx.doi.org/10.1021/jacs.9b09496
Descripción
Sumario:[Image: see text] Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.