Palladium-catalyzed C-C coupling under thermomorphic conditions Academic Article uri icon


  • Liquid-liquid biphasic systems that exhibit an increase in phase miscibility at elevated temperature together with soluble polymer-bound catalysts that have a strong phase preference at ambient temperature are described. In such systems, product isolation and catalyst recovery are effected by a liquid/liquid separation. This report describes the use of such thermomorphic catalyst recovery systems for palladium-catalyzed carbon-carbon bond forming reactions. Poly(N-isopropylacrylamide) (PNIPAM)-bound phosphine ligands with a Pd(0) catalyst used previously in allylic substitution chemistry are efficient catalysts in Heck, Suzuki, and sp-sp2 cross-coupling reactions. Air-stable tridentate SCS-Pd(II) catalysts bound to PNIPAM or poly(ethylene glycol) (PEG) are also described. A particular advantage of these SCS catalysts is that no precautions against adventitious catalyst oxidation need be taken with the polymer-bound SCS-PdCl catalysts, thus avoiding time-consuming solvent purification and degassing protocols.

published proceedings


altmetric score

  • 6

author list (cited authors)

  • Bergbreiter, D. E., Osburn, P. L., Wilson, A., & Sink, E. M.

citation count

  • 254

complete list of authors

  • Bergbreiter, DE||Osburn, PL||Wilson, A||Sink, EM

publication date

  • September 2000