Photoredox decarboxylative 3-fluoroallylation of α-amino acids
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Date
2025
Authors
Semeniuk, Taylor
Challenger, Jacob
Dudas, Ty
Toporkov, Dennis
van Hoeve, Miriam D.
Hamel, Jean-Denys
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
The 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 CC 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.
Description
Open access article. Creative Commons Attribution 4.0 International license (CC BY 4.0) applies
Keywords
Allylic difluorides , Amino acids , C-C coupling , Monofluoroalkenes , Photocatalysis
Citation
Semeniuk, 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