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Synthesis of ?-Fluoro-?-Amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination.

ABSTRACT: 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 ?-fluoro-?-amino acid. By using a highly oxidizing organic photocatalyst, this process incorporates non-stabilized primary, secondary, and tertiary alkyl radicals derived from commercially available alkyltrifluoroborates to furnish a wide range of fluorinated unnatural amino acids.

SUBMITTER: Sim J

PROVIDER: S-EPMC6777868 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Synthesis of α-Fluoro-α-Amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination.

Sim Jaehoon J Campbell Mark W MW Molander Gary A GA

ACS catalysis 20190124 2

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 non-stabilized primary, secondary, and tertiary alkyl radicals derived from commercially available al ...[more]

PMID: 31588366

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