Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates. Issue 16 (15th March 2016)

• Record Type: Journal Article
• Authors: Zhang, Enxuan; Tang, Jiaze; Li, Suhua; Wu, Peng; Moses, John E.; Sharpless, K. Barry
• Is Part Of: Chemistry. Volume 22:Issue 16(2016)
• Page Start: 5692
• Page End: 5697
• Publication Date: 2016-03-15
• Subjects: chemoselectivity -- cross-coupling reactions -- fluorosulfates -- palladium -- polysubstituted pyridine -- Suzuki reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600167
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2 F2 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. Abstract : A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2 F2 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.