Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

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

doi:10.1002/chem.201600167

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

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

Biochemistry

Research output: Contribution to journal › Article › peer-review

66 Scopus citations

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> -OSO₂F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. 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> -OSO₂F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

Original language	English (US)
Pages (from-to)	5692-5697
Number of pages	6
Journal	Chemistry - A European Journal
Volume	22
Issue number	16
DOIs	https://doi.org/10.1002/chem.201600167
State	Published - Apr 11 2016

Keywords

Suzuki reaction
chemoselectivity
cross-coupling reactions
fluorosulfates
palladium
polysubstituted pyridine

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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title = "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> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. 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> -OSO2F> -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",

author = "Enxuan Zhang and Jiaze Tang and Suhua Li and Peng Wu and Moses, {John E.} and Sharpless, {K. Barry}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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doi = "10.1002/chem.201600167",

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T1 - Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

AU - Zhang, Enxuan

AU - Tang, Jiaze

AU - Li, Suhua

AU - Wu, Peng

AU - Moses, John E.

AU - Sharpless, K. Barry

PY - 2016/4/11

Y1 - 2016/4/11

N2 - 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> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. 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> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

AB - 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> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. 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> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

KW - Suzuki reaction

KW - chemoselectivity

KW - cross-coupling reactions

KW - fluorosulfates

KW - palladium

KW - polysubstituted pyridine

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Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

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Keywords

ASJC Scopus subject areas

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