Many studies have been carried out using phase-selectively soluble polymer-supported catalysts and reagents. Our past work has focused more specifically on alkane-soluble polymeric ligands that facilitate separation of catalysts from polar products that partition into a polar phase most often using polymer bound versions of ligands that strongly coordinate to transition metals. However, while ionic immobilization of catalysts on insoluble polymers using quaternary ammonium catalysts is known, there are few examples where quaternary ammonium salts that form solvent separated ion pairs are used to recycle catalysts using a very nonpolar heptane phase. This paper will describe how vinyl-terminated polyisobutylene (PIB), a commercially available, low cost, and non-toxic polymer, can be used to prepare heptane soluble quaternary ammonium salts that can be used to potentially recycle homogeneous catalysts. Several routes to these ionic ligands will be described along with qualitative and quantitative studies of the phase selective solubility of PIB-bound tetraalkylammonium dye salts and tetraalkylammonium perruthenate salts. Strategies that use these heptane soluble salts in solvent mixtures that involve liquid/liquid separations after either thermomorphic reactions or in latent biphasic chemistry will be described along with studies using polyolefins as solvents for these hydrocarbon species.

Polyisobutylene-supported quaternary ammonium salts as phase selectively soluble anchoring agents

247th National Meeting (2014)

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