BODIPY-Labeled Cyclobutanes by Secondary C(sp3 )-H Arylations for Live-Cell Imaging

Chemistry. 2019 Oct 1;25(55):12712-12718. doi: 10.1002/chem.201903461. Epub 2019 Sep 13.

Abstract

Arylated cyclobutanes were accessed by a versatile palladium-catalyzed secondary C(sp3 )-H activation, exploiting chelation assistance by modular triazoles. The C-H arylation led to cyclobutane natural product derivatives in a highly regioselective fashion, setting the stage for the easy access to novel fluorogenic boron-dipyrrin (BODIPY)-labeled probes for live-cell imaging.

Keywords: BODIPY; C(sp3)−H activation; cyclobutanes; labeling; triazoles.

MeSH terms

  • Boron
  • Boron Compounds
  • Catalysis
  • Cell Tracking / methods*
  • Chelating Agents / chemistry
  • Cyclobutanes / chemistry*
  • Molecular Structure
  • Optical Imaging / methods*
  • Palladium / chemistry
  • Triazoles / chemistry*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Chelating Agents
  • Cyclobutanes
  • Triazoles
  • Palladium
  • Boron