Journal
TETRAHEDRON
Volume 72, Issue 40, Pages 6031-6036Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.018
Keywords
Fluorination; Photochemistry; Amino acids; Peptides; Regioselectivity
Categories
Funding
- National Science Foundation (NSF) [CHE-1465131]
- Johns Hopkins
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1465131] Funding Source: National Science Foundation
Ask authors/readers for more resources
A visible light-sensitized benzylic sp(3) 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. (C) 2016 Published by Elsevier Ltd.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available