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

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

58 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.

Original language	English (US)
Journal	Chemistry - A European Journal
DOIs	https://doi.org/10.1002/chem.201600167
State	Accepted/In press - 2016
Externally published	Yes

Keywords

Chemoselectivity
Cross-coupling reactions
Fluorosulfates
Palladium
Polysubstituted pyridine
Suzuki reaction

ASJC Scopus subject areas

Chemistry(all)

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10.1002/chem.201600167

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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.",

keywords = "Chemoselectivity, Cross-coupling reactions, Fluorosulfates, Palladium, Polysubstituted pyridine, Suzuki reaction",

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

year = "2016",

doi = "10.1002/chem.201600167",

language = "English (US)",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

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

Y1 - 2016

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.

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.

KW - Chemoselectivity

KW - Cross-coupling reactions

KW - Fluorosulfates

KW - Palladium

KW - Polysubstituted pyridine

KW - Suzuki reaction

UR - http://www.scopus.com/inward/record.url?scp=84961267239&partnerID=8YFLogxK

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U2 - 10.1002/chem.201600167

DO - 10.1002/chem.201600167

M3 - Article

AN - SCOPUS:84961267239

SN - 0947-6539

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

Abstract

Keywords

ASJC Scopus subject areas

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