Functionalized Polyisobutylene and Liquid/Liquid Separations as a Method for Scavenging Transition Metals from Homogeneously Catalyzed Reactions Academic Article uri icon

abstract

  • © 2018 by the authors. Ethanedithiol-functionalized polyisobutylene was prepared in one step by a photoinitiated thiol-ene "click" reaction starting from ethanedithiol and polyisobutylene (PIB). The functionalized oligomer product was then used as a soluble sequestrant for transition metals. This PIB-bound thioether-thiol ligand is phase selectively soluble in alkanes and it quantitatively sequesters common transition metals like Cu2+ and Pd2+ into an alkane phase, separating them from polar solvents in a biphasic liquid/liquid separation. The chelating thioether-thiol ligand was also successfully used to remove Cu and Pd transition metal catalyst residues from products in crude reaction mixtures in both azide/alkyne click reactions and cross-coupling reactions using a liquid/liquid extraction. Separation efficiencies exceeding 95% and in many cases 99% were achieved.

author list (cited authors)

  • Chouikhi, D., Kulai, I., Bergbreiter, D. E., Al-Hashimi, M., & Bazzi, H. S.

citation count

  • 2

publication date

  • December 2018