Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

Zhang, E., Tang, J., Li, S., Wu, P., Moses, J. E., Sharpless, K. B. (April 2016) Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates. Chemistry, 22 (16). pp. 5692-7. ISSN 0947-6539 (Print)0947-6539

DOI: 10.1002/chem.201600167


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.

Item Type: Paper
Additional Information: 1521-3765 Zhang, Enxuan Tang, Jiaze Li, Suhua Wu, Peng Moses, John E Sharpless, K Barry P50 GM103368/GM/NIGMS NIH HHS/United States R01 GM117145/GM/NIGMS NIH HHS/United States Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Chemistry. 2016 Apr 11;22(16):5692-7. doi: 10.1002/chem.201600167. Epub 2016 Mar 15.
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 11 April 2016
Date Deposited: 08 Jan 2021 18:00
Last Modified: 08 Jan 2021 18:00
PMCID: PMC4929982

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