Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling.
Masakazu NamboJacky C-H YimLuiza B O FreitasYasuyo TaharaZachary T ArikiYuuki MaekawaDaisuke YokogawaCathleen M CruddenPublished in: Nature communications (2019)
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.
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