Photoredox-Catalyzed Deaminative Alkylation via C-N Bond Activation of Primary Amines
Melissa A. Ashley and Tomislav Rovis*
*Department of Chemistry, Columbia University, New York, New York 10027, United States, Email: tr2504columbia.edu
M. A. Ashley, T. Rovis, J. Am. Chem. Soc., 2020, 142, 18310-18316.
DOI: 10.1021/jacs.0c08595
see article for more reactions
Abstract
By condensing α-3° primary amines with an electron-rich aryl aldehyde, an oxidation and deprotonation event is enabled, which generates a key imidoyl radical intermediate. A subsequent β-scission event liberates alkyl radicals for coupling with electron-deficient olefins for the generation of unnatural γ-quaternary amino acids and other valuable synthetic targets.
see article for more examples
Key Words
α-amino acids, photochemistry
ID: J48-Y2020