A traceless perfluoroalkylsulfonyl (PFS) linker for the deoxygenation of phenols

[GRAPHICS] The synthesis of a novel perfluoroalkylsulfonyl (PFS) fluoride is described for use as a traceless linker in solid-phase organic synthesis. Attachment to the resin and subsequent coupling of a phenol affords a stable arylsulf onate that behaves as a support-bound aryl triflate. Palladium-mediated red uctive cleavage of a wide variety of phenols generated the parent arenes. T he resin-bound aryl triflate was shown to be stable to reductive amination conditions, and the traceless synthesis of Meclizine is reported.