Synthesis 2018; 50(09): 1914-1920
DOI: 10.1055/s-0036-1591541
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient and Inexpensive Route to Sulfonylated Pyridines via SNAr Reaction of Electron-Rich Pyridines by Iron Catalysis

Fei Chen
a   Department of Chemistry & Biochemistry, Concordia University, 7141 rue Sherbrooke O. H4B 1R6, Montréal, QC, Canada   Email: pat.forgione@concordia.ca
,
Franklin Chacón-Huete
a   Department of Chemistry & Biochemistry, Concordia University, 7141 rue Sherbrooke O. H4B 1R6, Montréal, QC, Canada   Email: pat.forgione@concordia.ca
,
Hassan El-Husseini
a   Department of Chemistry & Biochemistry, Concordia University, 7141 rue Sherbrooke O. H4B 1R6, Montréal, QC, Canada   Email: pat.forgione@concordia.ca
,
Pat Forgione*
a   Department of Chemistry & Biochemistry, Concordia University, 7141 rue Sherbrooke O. H4B 1R6, Montréal, QC, Canada   Email: pat.forgione@concordia.ca
b   Centre for Green Chemistry and Catalysis, Montréal, QC, Canada
› Author Affiliations
This work was funded by the Natural Sciences and Engineering Research Council (NSERC) of Canada and Le Fonds de Recherche Nature et technologies du Québec (FQRNT). Support was also kindly provided by Centre for Green Chemistry and Catalysis (CGCC), and Concordia University.
Further Information

Publication History

Received: 27 November 2017

Accepted after revision: 12 January 2017

Publication Date:
20 February 2018 (online)


Abstract

Sulfonylated pyridines were synthesized in moderate to excellent yields, with a wide scope of substituted pyridines and sulfinate salts as starting materials, by an iron-catalyzed SNAr reaction. This new methodology exhibits advantages for the synthesis of these useful substrates, such as the use of a readily available, inexpensive catalyst, prevention of the disproportionation of the sulfinate salts, and, more importantly, providing access to electron-rich pyridine substrates.

Supporting Information