title: Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins.
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.
authors.affiliation: †School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Fernando
authors.initials: F
authors.lastname: Fernández-Nieto
authors.affiliation: †School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Josep
authors.initials: J
authors.lastname: Mas Roselló
authors.affiliation: †School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Simone
authors.initials: S
authors.lastname: Lenoir
authors.affiliation: ‡Syngenta Ltd., Jealott's Hill Research Centre, Bracknell, Berkshire, RG42 6EY, U.K.
authors.forename: Simon
authors.initials: S
authors.lastname: Hardy
authors.affiliation: †School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D006827:Hydantoins / Q000138:chemical synthesis / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D006827:Hydantoins; D006847:Hydrocarbons, Iodinated; D010165:Palladium