Organic Letters
Organic Letters
5 years ago

Radical C–H Fluorination Using Unprotected Amino Acids as Radical Precursors

Radical C–H Fluorination Using Unprotected Amino Acids as Radical Precursors
Duy N. Mai, Ramon Martinez, Ryan D. Baxter, Alyssa M. Hua
We report a unique example of utilizing unprotected amino acids for benzylic C–H fluorination via a radical process. α-Aminoalkyl radicals are readily generated via oxidative decarboxylation of unprotected amino acids using a simple silver(I) catalyst and Selectfluor, which serves as both a mild oxidant and source of electrophilic fluorine. Mechanistic investigation shows that coordination of the unprotected amino acid plays a crucial role in lowering the oxidation potential of Ag(I), enabling oxidation under mild conditions. Mono- or difluorination is possible by controlling the stoichiometry of amino acid and fluorine source.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01188

DOI: 10.1021/acs.orglett.7b01188

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