D. Bume, C. Pitts, R. Jokhai
Oct 6, 2016
Citations
1
Influential Citations
36
Citations
Journal
Tetrahedron
Abstract
Abstract A visible light-sensitized benzylic sp3 C H fluorination protocol using dibenzosuberenone (5 mol %) and Selectfluor® is optimized for the direct functionalization of phenylalanine-like residues in short chain peptides. Amino acids, dipeptides, and tripeptides undergo benzylic fluorination with remarkable regioselectivity in the presence of protected basic, acidic, and nonpolar side chains (including those with tertiary sites). Additionally, protecting group compatibility, a gram scale application, and competition experiments were explored.