Polyisobutylene-supported N-heterocyclic carbene palladium catalysts

This paper describes how the nonpolar polymer polyisobutylene (PIB) can be used as a handle to prepare PIB-bound NHC ligands that are soluble in monophasic mixtures of mixed solvents but phase separable when such solvent systems are perturbed to be biphasic. The results here show that such PIB-bound NHC ligands can be used to synthesize useful palladium catalysts. In this paper, both PIB-bound analogs of an N,N′-bis(2,6-diisopropylphenyl) heterocyclic carbene and simpler N,N′-dialkyl heterocyclic carbene ligand were prepared and were successfully used to form palladium cross-coupling catalysts. The reactivity, recycling and reusability of these catalysts has been examined.

Graphical abstractStudies of polyisobutylene-bound phase-separable NHC–Pd cross-coupling catalysts are detailed.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Phase-separable polyisobutylene-bound NHC ligand synthesis. ► Recyclable Pd cross-coupling catalysts. ► Heptane-soluble Pd arylbromide amination catalyst.