The rapidly rising prevalence of fluorinated motifs in pharmaceutical compounds has spurred interest in the development of synthetic methods which allow for the efficient incorporation of such fluorinated groups into complex molecules. Two fluorinated functional groups of interest are the α–trifluoromethyl alkene and the gem-difluoroalkene, which are particularly sought after due to their properties as bioisoteres. Two orthogonal methods have been developed which allow rapid access to diversely functionalized α–trifluoromethyl alkenes. The first method relies on the development of a novel cross-coupling reagent, and the second pushes the boundaries of the capabilities of Peterson olefination chemistry. In addition to their utility as bioisoteres, α–trifluoromethyl alkenes also serve as a uniquely well-suited starting point for the synthesis of gem-difluoroalkenes. Photoredox catalysis via radical polar crossover enables the alkylation and arylation of α–trifluoromethyl alkenes to allow access to a library of diversified gem-difluoroalkenes.

Accessing challenging fluorinated motifs using photoredox catalysis and enabling technologies

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.