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The S N Ar arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both 19 F-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multiple nucleophilic side chains currently presents a challenge to the field. Herein, we demonstrate that employing 2,2,2-trifluoroethanol (TFE) as a solvent in peptide S N Ar reactions significantly improves nucleophile-selectivity when compared to N,N'-dimethylformamide (DMF).

2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation