Palladium-catalyzed difluoroalkylative carbonylation of styrenes toward difluoropentanedioates

The introduction of fluorine atoms into organic molecules is an attractive but challenging topic. In this work, an interesting palladium-catalyzed difluoroalkylative carbonylation of aryl olefins has been developed. A wide range of aryl olefins were transformed into the corresponding difluoropentanedioate compounds with good functional-group tolerance and excellent regioselectivity. Inexpensive ethyl bromodifluoroacetate acts both as a difluoroalkyl precursor and a nucleophile here. Additionally, a scale-up reaction was also performed successfully, and further transformations of the obtained product were shown as well.

Automated summary

The introduction of fluorine atoms into organic molecules is an attractive topic. This work developed an interesting palladium-catalyzed reaction to transform aryl olefins into difluoropentanedioate compounds with good functional-group tolerance and high regioselectivity. Ethyl bromodifluoroacetate acts as both a difluoroalkyl precursor and a nucleophile in this reaction. Additionally, successful scale-up reactions and further transformations of the obtained product were demonstrated.