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Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins
Fernando Fernández-Nieto1, Josep Mas Roselló1, Simone Lenoir1
1†School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Abstract:
Palladium(II) trifluoroacetate (5 mol %) catalyzes the C-arylation of N,N-disubstituted hydantoins by aryl iodides in good yield. The reaction proceeds through base-promoted enolization of the amino acid derived hydantoins, and the resulting 5,5-disubstituted hydantoins may be deprotected at one or both N atoms to yield biologically active structures or alternatively hydrolyzed to the parent α-aryl α-amino acids. The reaction is successful with a variety of parent amino acids and a range of electron-rich and electron-poor aryl iodides.
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