Photoredox decarboxylative 3-fluoroallylation of α-amino acids

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dc.contributor.authorSemeniuk, Taylor
dc.contributor.authorChallenger, Jacob
dc.contributor.authorDudas, Ty
dc.contributor.authorToporkov, Dennis
dc.contributor.authorvan Hoeve, Miriam D.
dc.contributor.authorHamel, Jean-Denys
dc.date.accessioned2025-10-30T17:34:09Z
dc.date.available2025-10-30T17:34:09Z
dc.date.issued2025
dc.descriptionOpen access article. Creative Commons Attribution 4.0 International license (CC BY 4.0) applies
dc.description.abstractThe photocatalytic decarboxylation of α-amino acids is an effective route to α-aminoalkyl radicals, which is also amenable to the derivatization of peptides through selective CC bond formation at the C-terminus. It is reported that, in the presence of an iridium photocatalyst, allylic difluorides are suitable radical traps to capture α-aminoalkyl radicals produced from α-amino acids, ultimately amounting to a defluorinative 3-fluoroallylation reaction. The catalytic system is applied to the derivatization of a wide breadth of N-protected amino acids and dipeptides in high yields, and the transformation displays great functional group tolerance. α-Amino acids of all substitution levels at the α-carbon led to the desired products in high yields. Post-functionalization of the monofluoroalkene-containing products reveals the potential to attain fluorine-containing organic compounds of greater complexity.
dc.description.peer-reviewYes
dc.identifier.citationSemeniuk, T., Challenger, J., Dudas, T., Toporkov, D., van Hoeve, M. D., & Hamel, J.-D. (2025). Photoredox decarboxylative 3-fluoroallylation of α-amino acids. European Journal of Organic Chemistry, 28(33), Article e202500519. https://hdl.handle.net/10133/6820
dc.identifier.urihttps://hdl.handle.net/10133/7208
dc.language.isoen
dc.publisherWiley
dc.publisher.departmentDepartment of Chemistry and Biochemistry
dc.publisher.facultyArts and Science
dc.publisher.institutionUniversity of Lethbridge
dc.publisher.urlhttps://hdl.handle.net/10133/6820
dc.subjectAllylic difluorides
dc.subjectAmino acids
dc.subjectC-C coupling
dc.subjectMonofluoroalkenes
dc.subjectPhotocatalysis
dc.titlePhotoredox decarboxylative 3-fluoroallylation of α-amino acids
dc.typeArticle
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