Macromolecular Rapid Communications
Macromolecular Rapid Communications
5 years ago

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

Phase-Separable Polyisobutylene Palladium-PEPPSI Precatalysts: Synthesis and Application in Buchwald–Hartwig Amination
Dalila Chouikhi, Muhammad Ghufran Rafique, Hassan S. Bazzi, Ibrahim El-Zoghbi, Antsar Rih Hlil, Mohammed Al-Hashimi, Janos Balogh
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. Polyisobutylene-supported palladium PEPPSI is used for Buchwald–Hartwig amination of aryl chlorides.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/marc.201700214

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