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

ABSTRACT: 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.

SUBMITTER: Nambo M

PROVIDER: S-EPMC6778098 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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

Nambo Masakazu M Yim Jacky C-H JC Freitas Luiza B O LBO Tahara Yasuyo Y Ariki Zachary T ZT Maekawa Yuuki Y Yokogawa Daisuke D Crudden Cathleen M CM

Nature communications 20191004 1

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 triflo ...[more]

PMID: 31586048

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