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Synthesis of α‑Fluoro-α-amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination

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posted on 24.01.2019, 18:40 authored by Jaehoon Sim, Mark W. Campbell, Gary A. Molander
A mild, metal-free, regioselective carbofluorination of dehydroalanine derivatives has been developed. Alkyl radicals resulting from visible-light photoredox catalysis engage in a radical conjugate addition to dehydroalanine, with subsequent fluorination of the newly generated radical to afford an α-fluoro-α-amino acid. By using a highly oxidizing organic photocatalyst, this process incorporates nonstabilized primary, secondary, and tertiary alkyl radicals derived from commercially available alkyltrifluoroborates to furnish a wide range of fluorinated unnatural amino acids.