Photoredox Decarboxylative 3‐Fluoroallylation of α‐Amino Acids

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.