Ionic Liquids as Solvents for The Synthesis of N9-Modified C8-Adenine Adducts of Arylamines Using Palladium Catalysis
LaFrate, Andrew L.
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The study of modified nucleosides has traditionally been limited due to difficult, low yielding reactions, but Schoffers et al. developed an effective palladium-catalyzed synthesis of C8-adenosine adducts. The research described in this thesis focused on further investigating the Buchwald-Hartwig type reactions used by the Schoffers group by coupling modified bromoadenine with arylamines using palladium catalysis. The effects of various substituents at the N9 position ofthe adenine were investigated for these reactions. The efficacy of room temperature ionic liquids (RTILs) as solvents for the coupling reactions was also investigated. Traditional volatile organic compounds (VOCs) as solvents for reactions present many environmental hazards and can be difficult to work with because of their low boiling points. Recently RTILs have experienced an increase in popularity as solvents because oftheir high boiling points and thermal stability as well as their ability to be recycled after being used in a reaction, thus reducing negative effects on the environment. Ionic liquids are of particular interest as solvents for transition metal-catalyzed reactions because the catalyst and ligand are typically very expensive, but RTILs allow them to be recovered and used in successive reactions. Ionic liquids can also be custom-tailored to a particular system by varying the cation or anion, affecting their miscibility in other solvents and rendering them useful for liquid-liquid extractions.Administrator only at the request of the author 1/22/2015.