Palladium catalyzed carbon-carbon or carbon-heteroatom bond forming reactions have gained considerable attention and use over the last few decades. However, the use of expensive and hazardous organic solvents and rare, potentially toxic metals presents challenges to large-scale application of these methodologies. One possible way to address these challenges is through the use of water-soluble phosphine ligands that can facilitate catalyst recycling through phase separation, while reducing the need for organic solvents. It is known that sterically demanding, electron-rich phosphine ligands allow for highly active palladium catalysts. Bulky, electron-rich tri-alkyl phosphines, such as 3-(di-tert-butylphosphonium)propane sulfonate (DTBPPS), with hydrophilic substituents have been previously synthesized in our group and were shown to provide effective catalysts for cross-coupling reactions of aryl bromides and chlorides.  The design of new water-soluble phosphine ligands and their application in palladium-catalyzed reactions will be presented.

Synthesis and application of new water-soluble phosphine ligands in palladium-catalyzed reactions

245th National Meeting (2013)

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