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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


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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.


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Key Words

α-amino acids, photochemistry


ID: J48-Y2020