Premium
Phase‐Separable Polyisobutylene Palladium‐PEPPSI Precatalysts: Synthesis and Application in Buchwald–Hartwig Amination
Author(s) -
Balogh Janos,
Hlil Antsar Rih,
ElZoghbi Ibrahim,
Rafique Muhammad Ghufran,
Chouikhi Dalila,
AlHashimi Mohammed,
Bazzi Hassan S.
Publication year - 2017
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700214
Subject(s) - palladium , amination , heptane , chemistry , toluene , aryl , coupling reaction , solvent , organic chemistry , polymer chemistry , catalysis , alkyl
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.