Work

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

Year: 2016

Type: article

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.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201600167

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

Institutions: Tianjin Economic-Technological Development Area, Scripps Research Institute, University of Nottingham

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G2227661798, G345001416