4.8 Article

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

Journal

NATURE COMMUNICATIONS
Volume 10, Issue -, Pages -

Publisher

NATURE PUBLISHING GROUP
DOI: 10.1038/s41467-019-11758-w

Keywords

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Funding

  1. KAKENHI from JSPS [17K17805]
  2. JSPS through The World Premier International Research Center Initiative (WPI) program
  3. NU through The World Premier International Research Center Initiative (WPI) program
  4. Natural Sciences and Engineering Research Council of Canada (NSERC)
  5. Canada Foundation for Innovation (CFI)
  6. Ontario government
  7. Grants-in-Aid for Scientific Research [17K17805] Funding Source: KAKEN

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alpha-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 alpha-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of alpha-fluorinated benzylic triflones with arylboronic acids affording structurally diverse alpha-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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