4.1 Article

The Suzuki-Miyaura reaction of BPin-substituted F-BODIPYs with aryl halides

Journal

CANADIAN JOURNAL OF CHEMISTRY
Volume 99, Issue 3, Pages 287-294

Publisher

CANADIAN SCIENCE PUBLISHING
DOI: 10.1139/cjc-2020-0300

Keywords

late-stage F-BODIPY arylation; aryl halides; BPin-substituted F-BODIPYs

Funding

  1. NSERC of Canada
  2. NSERC of Canada via CREATE Training Program in BioActives [510963]

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The method described in the text involves coupling BPin-substituted F-BODIPYs to aryl halides using a mild and efficient catalyst system, enabling the preparation of highly functionalised F-BODIPYs without the need for the corresponding aryl moiety to be in borylated form.
F-BODIPYs substituted with BPin functionality have been coupled to aryl halides using a mild and efficient catalyst system involving Pd-2(dba)(3) and XPhos. The methodology enables the Suzuki-Miyaura cross-coupling of electron-rich, electron-poor, and sterically encumbered BPin-substituted F-BODIPYs to aryl halides bearing various functional groups, thus presenting an opportunity for the preparation of highly functionalised F-BODIPYs without need for the corresponding aryl moiety to be available in borylated form.

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