Details

Autor(en) / Beteiligte

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

Titel

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

Ist Teil von

• Chemistry : a European journal, 2016-04, Vol.22 (16), p.5692-5697

Ort / Verlag

Germany: Blackwell Publishing Ltd

Erscheinungsjahr

2016

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• 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.