[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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http://dx.doi.org/10.1021/ol0163732 | DOI Listing |
Angew Chem Int Ed Engl
December 2001
Department of Chemistry, Affymax Research Institute 4001 Miranda Avenue, Palo Alto, CA 94304 (USA).
Org Lett
August 2001
Affymax Research Institute, 4001 Miranda Avenue, Palo Alto, California 94304, USA.
[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.
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