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Issue 19, 2017
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2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

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Abstract

The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both 19F-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 SNAr reactions significantly improves nucleophile-selectivity when compared to N,N′-dimethylformamide (DMF).

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

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Publication details

The article was received on 07 Feb 2017, accepted on 19 Apr 2017 and first published on 21 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00295E
Citation: Org. Biomol. Chem., 2017,15, 4081-4085
  • Open access: Creative Commons BY license
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    2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

    D. Gimenez, A. Dose, N. L. Robson, G. Sandford, S. L. Cobb and C. R. Coxon, Org. Biomol. Chem., 2017, 15, 4081
    DOI: 10.1039/C7OB00295E

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