3,4,5-Trifluorophenyldiazonium – a unique radical source for the visible light induced, catalyst-free arylation of tyrosine residues in peptides

Heinrich M, Kuschow M, Troeger D, Schuster LS, Bock L, Zähnle L (2025)

Publication Type: Journal article

Publication year: 2025

Journal

DOI: 10.1002/chem.202501160

Abstract

The direct radical arylation of tyrosine residues in peptides has been achieved under highly attractive conditions, requiring only the peptide substrate, a 3,4,5-trifluorophenyldiazonium salt and irradiation with visible light. Being well-balanced in its reactivity to form strong charge transfer complexes with the phenolic side chain, which are required for initiation and aryl radical formation, the trifluoro substitution still shows sufficient stability towards nucleophilic aromatic substitution in aqueous solution. Besides allowing selective arylation, the introduction of the 3,4,5-trifluorophenyl unit enables further functionalization as well as potential applications in NMR and MRT studies.

Authors with CRIS profile

Markus Heinrich Professur für Pharmazeutische Chemie Meret Kuschow Lehrstuhl für Pharmazeutische Chemie Daniel Troeger Lehrstuhl für Pharmazeutische Chemie Luca Sophie Schuster Lehrstuhl für Pharmazeutische Chemie Leonard Bock Lehrstuhl für Pharmazeutische Chemie Leon Zähnle Lehrstuhl für Pharmazeutische Chemie

How to cite

APA:

Heinrich, M., Kuschow, M., Troeger, D., Schuster, L.S., Bock, L., & Zähnle, L. (2025). 3,4,5-Trifluorophenyldiazonium – a unique radical source for the visible light induced, catalyst-free arylation of tyrosine residues in peptides. Chemistry - A European Journal. https://doi.org/10.1002/chem.202501160

MLA:

Heinrich, Markus, et al. "3,4,5-Trifluorophenyldiazonium – a unique radical source for the visible light induced, catalyst-free arylation of tyrosine residues in peptides." Chemistry - A European Journal (2025).

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