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

Masakazu Nambo (), Jacky C.-H. Yim, Luiza B. O. Freitas, Yasuyo Tahara, Zachary T. Ariki, Yuuki Maekawa, Daisuke Yokogawa and Cathleen M. Crudden ()
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Masakazu Nambo: Nagoya University
Jacky C.-H. Yim: Nagoya University
Luiza B. O. Freitas: Queen’s University
Yasuyo Tahara: Nagoya University
Zachary T. Ariki: Queen’s University
Yuuki Maekawa: Queen’s University
Daisuke Yokogawa: The University of Tokyo
Cathleen M. Crudden: Nagoya University

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-11758-w

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