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Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates
April 11 2016
April 11 2016
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Abstract
<p class="first" id="P1">A selection of
<b>heteroaryl</b> fluorosulfates were readily synthesized using commercial SO
<sub>2</sub>F
<sub>2</sub> gas. These substrates are highly efficient coupling partners in the Suzuki
reaction.
Through judicious selection of Pd-catalysts, the fluorosulfate functionality is differentiated
from bromide and chloride; the order of reactivity being: -Br > -OSO
<sub>2</sub>F > -Cl. Exploiting this trend allowed the stepwise chemoselective
synthesis of a
number of polysubstituted pyridines, including the drug, Etoricoxib.
</p><p id="P2">
<div class="figure-container so-text-align-c">
<img alt="" class="figure" src="/document_file/42d2f6c9-8276-42fe-bb0d-9c2bf1ecb6fd/PubMedCentral/image/nihms782172u1.jpg"/>
</div>
</p>
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