Highly Recoverable Pd(II) Catalysts for the Mizoroki–Heck
Reaction Based on N‑Heterocyclic Carbenes and Poly(benzyl ether)
Dendrons
Posted on 2018-07-18 - 18:43
Two series of bis(imidazolylidene)palladium
complexes of general
formula [PdBr2(NHC)2] have been prepared. The
molecular weight of the complexes was enlarged by bonding poly(benzyl
ether) dendrons of increasing size (G0 to G3) at the nitrogen atom
of the NHC ligands. Complexes 1–4 contain monodentate NHC ligands coordinated in a trans mode, whereas complexes 9–12 contain
a chelating ethylene-bridged bis(NHC) ligand. The complexes were recovered
from the product stream of a Mizoroki–Heck reaction by nanofiltration
through thermally and chemically stable ceramic membranes. The recoverability
is better for larger complexes and chelate ligands. In particular,
chelate G3 complex 12 maintained a constant activity
during the 13 recovery cycles performed, affording an accumulated
turnover number (TON) of 13 000. On average, around 99.5% of
the metal is recovered in each recovery cycle, and contamination by
palladium is only 3 mg per kg of product. Several models to explain
the efficiency of the recovery are discussed.
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Ortiz, Alba; Gómez-Sal, Pilar; Flores, Juan C.; Jesús, Ernesto de (2018). Highly Recoverable Pd(II) Catalysts for the Mizoroki–Heck
Reaction Based on N‑Heterocyclic Carbenes and Poly(benzyl ether)
Dendrons. ACS Publications. Collection. https://doi.org/10.1021/acs.organomet.8b00295
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AUTHORS (4)
AO
Alba Ortiz
PG
Pilar Gómez-Sal
JF
Juan C. Flores
EJ
Ernesto de Jesús