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3,4,5‐Trifluorophenyldiazonium–A Unique Radical Source for the Visible Light Induced, Catalyst‐Free Arylation of Tyrosine Residues in Peptides

Year: 2025

Type: article

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 toward 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.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202501160

Authors: Meret K. Kuschow, Daniel R. Troeger, Luca‐Sophie Schuster, Leonard Bock, Leon A. Zähnle, Markus R. Heinrich

Institution: Friedrich-Alexander-Universität Erlangen-Nürnberg

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funder: Deutsche Forschungsgemeinschaft