Synthesis of Polymer-Bound 4-acetoxy-3-phenylbenzaldehyde Derivatives: Applications in Solid-Phase Organic Synthesis
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.
Kumar, Anil, Guofeng Ye, Yousef Ahmadibeni, and Keykavous Parang. "Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: Applications in solid-phase organic synthesis." The Journal of organic chemistry 71, no. 20 (2006): 7915-7918.
American Chemical Society