Introduction of two polyvinyl alcohol resins for efficient solid support Cu‐catalyzed N‐arylation of α‐aminoacids with aryl halides in aqueous media

Abstract

ABSTRACTIn this article, two polyvinyl alcohol (PVA)‐based resins were prepared by crosslinking of epoxidized PVA‐chains using of 4‐(4‐aminobenzyl)benzenamine as a crosslinker and polymerization of acrylated PVA chains in the another approach. The prepared PVA resins showed well hydrophilic and swelling properties in various organic solvents, which are used in solid‐phase organic synthesis (SPOS). Swelling properties of these resins were examined in dimethylformamide, tetrahydrofuran, water, ethanol, methanol, dichloromethane, and dioxane. Furthermore, the both resins were characterized by FTIR and 1H‐NMR and their properties such as epoxy equivalent weight (EEW) of epoxidized PVA and density of the resins were determined by analytical methods. Then, α‐amino acids such as L‐aspartic acid, L‐leucine, L‐alanine, L‐serine, L‐valine, L‐threonine, and L‐tyrosine were immobilized on both resins through esterification reaction between these α‐amino acids with the present hydroxyl groups on PVA resines, to carry out their solid‐phase N‐arylation reaction in the presence of CuI as a catalyst in milder and greener conditions than free resin protocols. Hydrolysis of the correponding N‐arylated α‐amino acids immobilized on the resins gave the N‐arylated α‐amino acids in high to excellent yields. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47597.