C−H Fluoromethoxylation of Arenes by Photoredox Catalysis

Redox‐active N‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradia...

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Detalles Bibliográficos
Autores principales: Bertoli, Giulia, Martínez, Ángel Manu, Goebel, Jonas F., Belmonte, Debora, Sivendran, Nardana, Gooßen, Lukas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107189/
https://www.ncbi.nlm.nih.gov/pubmed/36385731
http://dx.doi.org/10.1002/anie.202215920
Descripción
Sumario:Redox‐active N‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradiation of 1‐(OCH(2)F)‐3‐Me‐6‐(CF(3))benzotriazolium triflate with blue LED light in the presence of [Ru(bpy)(3)(PF(6))(2)] promotes the synthesis of diversely functionalized aryl monofluoromethyl ethers. This method allows the late‐stage functionalization of biologically relevant structures without relying on ecologically problematic halofluorocarbons.

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