Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Enxuan Zhang, Jiaze Tang, Suhua Li, Peng Wu, John E Moses, K Barry Sharpless

Chemistry (Weinheim an der Bergstrasse, Germany) 2016 Apr 11

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A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 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> -OSO2 F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Enxuan Zhang, Jiaze Tang, Suhua Li, Peng Wu, John E Moses, K Barry Sharpless. Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates. Chemistry (Weinheim an der Bergstrasse, Germany). 2016 Apr 11;22(16):5692-7