Suzuki–Miyaura
Coupling Reactions of Iodo(difluoroenol)
Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient
Temperatures
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Abstract
A recently developed method for the near-ambient generation
of
difluorovinylzinc reagents has facilitated the preparation of 1-(<i>N</i>,<i>N</i>-diethylcarbamoyloxy)-2,2-difluoro-1-iodoethene
and 2,2-difluoro-1-iodo-1-(2′-methoxyethoxymethoxy)ethene.
The utility of these reagents has been investigated in Suzuki–Miyaura
couplings with a range of potassium trifluoroborate coupling partners,
with the scope of successful couplings proving wide. Deiodinated species
appeared as significant side products, but a solvent change from <i>i</i>-PrOH to <i>t</i>-BuOH suppressed the pathway
to these species and improved coupling yields