TY - JOUR
T1 - Phase-Separable Polyisobutylene Palladium-PEPPSI Precatalysts
T2 - Synthesis and Application in Buchwald–Hartwig Amination
AU - Balogh, Janos
AU - Hlil, Antsar Rih
AU - El-Zoghbi, Ibrahim
AU - Rafique, Muhammad Ghufran
AU - Chouikhi, Dalila
AU - Al-Hashimi, Mohammed
AU - Bazzi, Hassan S.
N1 - Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/8
Y1 - 2017/8
N2 - 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.
AB - 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.
KW - Buchwald–Hartwig amination
KW - N-heterocyclic carbenes (NHCs)
KW - aryl chlorides
KW - palladium-PEPPSI
KW - supported catalysts
UR - http://www.scopus.com/inward/record.url?scp=85020492044&partnerID=8YFLogxK
U2 - 10.1002/marc.201700214
DO - 10.1002/marc.201700214
M3 - Article
C2 - 28627077
AN - SCOPUS:85020492044
SN - 1022-1336
VL - 38
JO - Macromolecular Rapid Communications
JF - Macromolecular Rapid Communications
IS - 15
M1 - 1700214
ER -