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> -OSO2 F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.
authors.affiliation: Asymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China. zhangenxuan@asymchem.com.cn.
authors.forename: Enxuan
authors.initials: E
authors.lastname: Zhang
authors.affiliation: Asymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China.
authors.forename: Jiaze
authors.initials: J
authors.lastname: Tang
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Suhua
authors.initials: S
authors.lastname: Li
authors.affiliation: Department of Chemical Physiology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Peng
authors.initials: P
authors.lastname: Wu
authors.affiliation: School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
authors.forename: John E
authors.initials: JE
authors.lastname: Moses
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA. sharples@scripps.edu.
authors.forename: K Barry
authors.initials: KB
authors.lastname: Sharpless
mesh_terms: D002384:Catalysis; D000077613:Etoricoxib; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011725:Pyridines; D013450:Sulfones; D010165:Palladium; D000077613:Etoricoxib
keywords: Suzuki reaction; chemoselectivity; cross-coupling reactions; fluorosulfates; palladium; polysubstituted pyridine