One-Pot, Two-Step, Microwave-Assisted Palladium-Catalyzed Conversion of Aryl Alcohols to Aryl Fluorides via Aryl Nonaflates
2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 8, 4184-4189 p.Article in journal (Refereed) Published
A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.
Place, publisher, year, edition, pages
2013. Vol. 78, no 8, 4184-4189 p.
Medical and Health Sciences Natural Sciences
IdentifiersURN: urn:nbn:se:uu:diva-203361DOI: 10.1021/jo400255mISI: 000319708300024OAI: oai:DiVA.org:uu-203361DiVA: diva2:636341