Synthesis of Polymer-Bound 4-acetoxy-3-phenylbenzaldehyde Derivatives: Applications in Solid-Phase Organic Synthesis

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Aminomethyl polystyrene resin was reacted with 4-(5‘-formyl-2‘-hydroxyphenyl)benzoic acid and 4-(5‘-formyl-2‘-hydroxyphenyl)phenyl propionic acid, respectively, in the presence of 1-hydroxybenzotriazole and 1,3-diisopropylcarbodiimide to yield polymer-bound benzaldehydes. The phenolic group in resins was acetylated with acetic anhydride to afford two polymer-bound 4-acetoxybenzaldehydes. The reductive amination of polymer-bound linkers by amines and sodium triacetoxyborohydride, followed by sulfonylation with arylsulfonyl chloride derivatives in the presence of pyridine and the cleavage with TFA/DCM/H2O, produced pure sulfonamides.


This is a pre-copy-editing, author-produced PDF of an article accepted for publication in The Journal of Organic Chemistry, volume 71, issue 20, 2006 following peer review. The definitive publisher-authenticated version is available online at DOI: 10.1021/jo061328z.


American Chemical Society