Hamel, Jean-Denys

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Photoredox decarboxylative 3-fluoroallylation of α-amino acids
(Wiley, 2025) Semeniuk, Taylor; Challenger, Jacob; Dudas, Ty; Toporkov, Dennis; van Hoeve, Miriam D.; Hamel, Jean-Denys
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 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.