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Chemistry. 2016 Apr 11;22(16):5692-7. doi: 10.1002/chem.201600167. Epub 2016 Mar 15.

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Author information

1
Asymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China. zhangenxuan@asymchem.com.cn.
2
Asymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China.
3
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
4
Department of Chemical Physiology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
5
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
6
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA. sharples@scripps.edu.

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.

KEYWORDS:

Suzuki reaction; chemoselectivity; cross-coupling reactions; fluorosulfates; palladium; polysubstituted pyridine

PMID:
26990693
PMCID:
PMC4929982
DOI:
10.1002/chem.201600167
[Indexed for MEDLINE]
Free PMC Article

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