Synthesis of Alkyl Fluorides and Fluorinated Unnatural Amino Acids via Photochemical Decarboxylation of α-Fluorinated Carboxylic Acids

Leveraging alpha-fluoroalkyl or fluorobenzyl radicals to introduce fluorinated motifs allows for the rapid preparation of fluorine-containing building blocks. Herein, we report the generation of alpha-fluoroalkyl or fluorobenzyl radicals from readily available alpha-fluorocarboxylic acids under mild reaction conditions and their utilization in the Giese-type addition on Michael acceptors and dehydroamino acids, resulting in the preparation of mono-and difluorinated Michael addition adducts and unnatural fluorinated amino acids.

Automated summary

Using alpha-fluoroalkyl or fluorobenzyl radicals generated from easily accessible alpha-fluorocarboxylic acids, we achieved the rapid synthesis of fluorine-containing building blocks through Giese-type addition reactions. This method allows for the preparation of mono- and difluorinated Michael addition adducts as well as unnatural fluorinated amino acids under mild reaction conditions.