4.3 Article

Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 179, Issue -, Pages 106-115

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2015.06.008

Keywords

Catalyst; Fluoroalkenes; Packing; Palladium; Polycyclic aromatic hydrocarbons; Semiconductors

Funding

  1. JSPS KAKENHI [25288016, 2562015]
  2. Asahi Glass Foundation
  3. Grants-in-Aid for Scientific Research [15K05414, 26105705, 25288016] Funding Source: KAKEN

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Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by pi-pi and C-H center dot center dot center dot F interactions to exhibit columnar and layer structures in the solid state. (C) 2015 Elsevier B.V. All rights reserved.

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