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Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

ABSTRACT: 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.

SUBMITTER: Zhang E

PROVIDER: S-EPMC4929982 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Zhang Enxuan E Tang Jiaze J Li Suhua S Wu Peng P Moses John E JE Sharpless K Barry KB

Chemistry (Weinheim an der Bergstrasse, Germany) 20160315 16

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. ...[more]

PMID: 26990693

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