Photocatalytic Decarboxylative Coupling of Aliphatic N-Hydroxyphthalimide Esters with Bromopolyfluorobenzene

We describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters with bromopolyfluorobenzene enabled by the synergetic action of Hantzsch ester, photoredox catalyst, and nickel catalyst. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding polyfluoroaryl compounds with broad scope and excellent functional group compatibility. The practicality of this method was further demonstrated by the direct modification of amino acids and biologically active molecules.

Automated summary

We have developed a decarboxylative coupling reaction between N-hydroxyphthalimide esters and bromopolyfluorobenzene, which is facilitated by the synergetic action of Hantzsch ester, photoredox catalyst, and nickel catalyst. This method allows for the efficient conversion of primary and secondary alkyl carboxylic acids into polyfluoroaryl compounds, demonstrating broad scope and excellent functional group compatibility. Furthermore, we have successfully demonstrated the applicability of this method in the direct modification of amino acids and biologically active molecules.