Phase-Separable Polyisobutylene Palladium-PEPPSI Precatalysts: Synthesis and Application in Buchwald–Hartwig Amination

Janos Balogh, Antsar Rih Hlil, Ibrahim El-Zoghbi, Muhammad Ghufran Rafique, Dalila Chouikhi, Mohammed Al-Hashimi, Hassan S. Bazzi

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Abstract

This paper reports the efficient synthesis of the first class of polyisobutylene(PIB)-supported palladium-PEPPSI precatalyst (PEPPSI = pyridine-enhanced precatalyst preparation, stabilization, and initiation). The new complexes are employed in Buchwald–Hartwig amination of aryl chlorides and are found to be reasonably active in the titled cross-coupling reaction. The supported catalysts are tested in polar (1,4-dioxane and 1,2-dimethoxyethane) as well as in aliphatic reaction media (toluene and n-heptane) and display superior activity in the highly lipophilic solvent (n-heptane). The catalytic efficacy of PIB-Pd-PEPPSI precatalyst is measured to be comparable to its nonsupported analog. Pd-leaching is determined by inductively coupled plasma mass spectrometry (ICP-MS) after a simple liquid/liquid extraction and is found to be 2 ppb in the product phase, translating into a recovery of ≈99.8% of the palladium.

Original languageEnglish
Article number1700214
JournalMacromolecular Rapid Communications
Volume38
Issue number15
DOIs
Publication statusPublished - 1 Aug 2017

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Keywords

  • aryl chlorides
  • Buchwald–Hartwig amination
  • N-heterocyclic carbenes (NHCs)
  • palladium-PEPPSI
  • supported catalysts

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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