A traceless perfluoroalkylsulfonyl (PFS) linker for the deoxygenation of phenols.
[reaction: see text]. 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 arylsulfonate that behaves as a support-bound aryl triflate. Palladium-mediated reductive cleavage of a wide variety of phenols generated the parent arenes. The resin-bound aryl triflate was shown to be stable to reductive amination conditions, and the traceless synthesis of Meclizine is reported.
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Affymax Research Institute, 4001 Miranda Avenue, Palo Alto, California 94304, USA.
Holmes
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