Micellar Palladium Catalyst Stabilized by PEG-PVEG as a Vinyl-Functionalized Amphiphilic Polymer for Suzuki-Miyaura Coupling in Water

Abstract

An easily made and highly efficient vinyl-functionalized amphiphilic polymer, polyethylene glycol-polyvinylethylene glycol (PEG-PVEG), designed based on the metal-olefin interactions, has been developed via one-step allylic etherification polymerization. The superior performance of PEG-PVEG was demonstrated in aqueous Suzuki-Miyaura coupling of diverse substrates, facilitated by various palladium catalysts with very high efficiency. This effectiveness was further validated through gram-scale transformations, API intermediates synthesis, and recycling studies. The remarkable achievement stems from the self-assembly of PEG-PVEG, which not only provides a hydrophobic microenvironment for reactions but also stabilizes palladium catalysts via vinyl groups in micelles, as confirmed by 31P NMR analysis and control experiments.