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Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-cat...

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Detalles Bibliográficos
Autores principales: Nambo, Masakazu, Yim, Jacky C.-H., Freitas, Luiza B. O., Tahara, Yasuyo, Ariki, Zachary T., Maekawa, Yuuki, Yokogawa, Daisuke, Crudden, Cathleen M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6778098/
https://www.ncbi.nlm.nih.gov/pubmed/31586048
http://dx.doi.org/10.1038/s41467-019-11758-w
Descripción
Sumario:α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.