A panel of heteroaryl fluorosulfates was synthesized using sulfuryl fluoride via the Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry. These fluorosulfates were employed as coupling partners in the Pd-catalyzed Suzuki−Miyaura reaction. By using different Pd catalysts, the fluorosulfate functionality can be differentiated from bromide and chloride, in which the order of reactivity is -Br &gt; -OSO<sub>2</sub>F &gt; -Cl. On the basis of this observed chemoselectivity, drug Etoricoxib and tri-aryl-substituted pyridines were prepared in high yields from the corresponding -Br, -OSO<sub>2</sub>F and -Cl substituted pyridines by sequential Suzuki coupling reactions.

Suzuki-Miyaura couplings with SuFEx-derived heteroaryl fluorosulfates

251st National Meeting (2016)

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