Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins

Fernando Fernández-Nieto, Josep Mas Roselló, Simone Lenoir, Simon Hardy, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

27 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)3838-3841
Number of pages4
JournalOrganic Letters
Issue number15
Early online date22 Jul 2015
Publication statusPublished - 7 Aug 2015


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