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Designing Phase Selectively Soluble Polymer-Supports for Dimethylaminopyridine and Phosphine-Ligated Pd(0) Catalysts

Abstract

Soluble poly(4-alkylstyrene) containing 4-methyl-, 4-tert-butyl, 4-dodecyl-, and 4-octadecylstyrene were formed either with monomers containing dyes-, ligands, or catalysts or with 5–10 mol% of 4-chloromethylstyrene and studied as supports for ligands or catalysts. Studies with dye-labeled polymers showed that polymers containing longer alkyl groups alone or at ca. 10 mol% loading are highly soluble in heptane can be used to separate and recycle organo- and transition metal catalysts.

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Acknowledgments

We gratefully acknowledge support by the Qatar National Research Fund (Project Number 4-081-1-016) for the studies of separable Pd(0) catalysts and the Robert A. Welch Foundation (Grant A-0639) for studies of poly(4-alkylstyrene) solubility and its use in organocatalysis. Mr. Jakkrit Suriboot is thanked for his assistance in the ICP-MS analysis of the Pd leaching.

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Correspondence to David E. Bergbreiter.

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Khamatnurova, T.V., Johnson, M., Santana, D. et al. Designing Phase Selectively Soluble Polymer-Supports for Dimethylaminopyridine and Phosphine-Ligated Pd(0) Catalysts. Top Catal 57, 1438–1444 (2014). https://doi.org/10.1007/s11244-014-0315-3

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Keywords

  • Dimethylaminopyridine
  • Phosphine
  • Palladium
  • Suzuki
  • Recycling
  • Cross-coupling