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 journalArticle

45 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 languageEnglish (US)
JournalChemistry - A European Journal
DOIs
StateAccepted/In press - 2016
Externally publishedYes

Keywords

  • Chemoselectivity
  • Cross-coupling reactions
  • Fluorosulfates
  • Palladium
  • Polysubstituted pyridine
  • Suzuki reaction

ASJC Scopus subject areas

  • Chemistry(all)

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