Synthesis and Reactivity of Acetonitrile-Solvated Trifluoromethyl Palladium Complexes
Introducing fluorine-containing groups into organic molecules can strongly influence their
chemical and physical properties. For this reason, the incorporation of groups like
trifluoromethyl (CF 3 ) into pharmaceuticals and agrochemicals has been especially popular in
recent years. One method that has proven challenging and perilous is the attachment of CF 3
groups to nitrogen. In this presentation, I will describe our efforts to use palladium for
transferring CF 3 groups into nitrogen-containing organic molecules. Preparation and study of a
series of acetonitrile-solvated palladium complexes containing multiple CF 3 groups were
prepared as reagents for new palladium-based methodologies. These compounds provide insight
into how solvated palladium complexes can support trifluoromethylation chemistry and reveal
new understanding of this class of organometallic complexes. We found that these solvated
palladium trifluoromethyl complexes react with nitrogen-containing compounds to form new
coordination complexes. Further reactivity studies show promise that these types of complexes
may be used to mediate nitrogen-CF 3 bond forming reactions. Overall, this work expands the
understanding of palladium-mediated trifluoromethylation and offers a safer, less hazardous
approach for building fluorinated molecules relevant to medicine and agriculture.