jo400255m_si_001.pdf (880.45 kB)
One-Pot, Two-Step, Microwave-Assisted Palladium-Catalyzed Conversion of Aryl Alcohols to Aryl Fluorides via Aryl Nonaflates
journal contribution
posted on 2013-04-19, 00:00 authored by Johan Wannberg, Charlotta Wallinder, Meltem Ünlüsoy, Christian Sköld, Mats LarhedA 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.