Synthesis, catalysis and recycling studies of perfluoroalkylated palladium complexes

A range of fluorous monodentate triarylphosphines were synthesised using novel chemistry and modified literature methods. the corresponding complexes were shown to be more active in the Suzuki reaction, compared with the non-fluorous derivative, triphenylphosphine. However, the catalysts simply decomposed under the reaction conditions to form palladium black making it impossible for these fluorous catalysts to be recycled.;The synthesis and coordination chemistry of fluorous and non-fluorous pincer phosphines has been investigated. Both palladium pincer catalysts successfully catalyse a range of Heck and Suzuki reactions. However, recovery and reuse was only possible with the fluorous pincer catalyst, which could be successfully recovered and reused three times in the Heck reaction with no loss in activity. In the Suzuki reaction, recovery and reuse of the fluorous pincer catalyst was possible, however, decomposition of the catalyst was detected under the reaction conditions leading to an inevitable loss in activity.;A range of fluorous and non-fluorous monodentate, bidentate and pincer NHC ligands and palladium complexes were synthesised using novel chemistry and modified literature methods. The monodentate NHC complexes were evaluated in Heck reactions. The recovery and reuse of the fluorous carbene complexes were evaluated with differing success. Under homogenous reaction conditions, decomposition of the light fluorous catalyst was detected upon recovery of the catalyst. Conversely, when supporting the heavily fluorinated carbene complex on Fluorous Reverse Phase Silica Gel (FRPSG), the catalyst was successful used three times. However, due to poor recovery of the support, inevitable loss in product conversion was observed.