Gimenez Diana, Dose Anica, Robson Nicholas L, Sandford Graham, Cobb Steven L, Coxon Christopher R
Durham University, Department of Chemistry, South Road, Durham, DH1 3LE, UK.
Org Biomol Chem. 2017 May 16;15(19):4081-4085. doi: 10.1039/c7ob00295e.
The SAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both 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 SAr reactions significantly improves nucleophile-selectivity when compared to N,N'-dimethylformamide (DMF).
肽与全氟芳烃的SAr芳基化反应提供了一种引入有用化学基团的途径，该基团可用于F-NMR分析和进一步的化学修饰。然而，在含有多个亲核侧链的肽中进行化学选择性芳基化目前仍是该领域面临的一个挑战。在此，我们证明，与N，N'-二甲基甲酰胺（DMF）相比，在肽的SAr反应中使用2,2,2-三氟乙醇（TFE）作为溶剂可显著提高亲核试剂的选择性。
