Amine Directed Palladium Catalyzed C‐H Halogenation of Phenylalanine Derivatives

Alexia Ville (1) , Julien Annibaletto (1) , Sébastien Coufourier (1, 2) , Christophe Hoarau (1) , Rodolphe Tamion (1) , Guillaume Journot (2) , Cédric Schneider (1) , Jean-François Brière (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Oril Industrie

An efficient primary amine-directed palladium catalyzed C-H halogenation (X = I, Br, Cl) of phenylalanine derivatives is reported on a range of quaternary amino acid (AA) derivatives thanks to suited conditions employing trifluoroacetic acid as additive. The extension of this original native functionality-directed ortho-selective halogenation was even demonstrated with the more challenging native phenylalanine as tertiary AA.

Mots clés: amino acids; CH functionalization; halogenation; homogenous catalysis; palladium

Domaines: Chimie organique; Catalyse

Alexia Ville, Julien Annibaletto, Sébastien Coufourier, Christophe Hoarau, Rodolphe Tamion, et al.. Amine Directed Palladium Catalyzed C‐H Halogenation of Phenylalanine Derivatives. Chemistry - A European Journal, inPress, 27, pp.13961-13965. ⟨10.1002/chem.202102411⟩. ⟨hal-03322472⟩