87324-13-8Relevant articles and documents
Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL
Bagherzadeh, Mojtaba,Mahmoudi, Hamed,Ataie, Saeed,Bahjati, Mohammad,Kia, Reza,Raithby, Paul R.,Vaccaro, Luigi
, (2019/06/05)
A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.
A tailored polymeric cationic tag-anionic Pd(ii) complex as a catalyst for the low-leaching Heck-Mizoroki coupling in flow and in biomass-derived GVL
Mahmoudi, Hamed,Valentini, Federica,Ferlin, Francesco,Bivona, Lucia Anna,Anastasiou, Ioannis,Fusaro, Luca,Aprile, Carmela,Marrocchi, Assunta,Vaccaro, Luigi
supporting information, p. 355 - 360 (2019/01/28)
The [PdCl4]2- palladium complex has been immobilized on a polystyrene-type resin loaded with pincer-type imidazolium ionic tag binding sites. The catalytic system (Pd(ii)-POLI-TAG) has proved to be highly active in the definition of an efficient protocol for the Heck-Mizoroki coupling reaction under batch and flow conditions. Importantly, it is shown to be highly robust in combination with a safe non-toxic reaction medium, i.e. biomass-derived GVL, since it could be reused for multiple runs without significantly losing its activity.
Synthesis and Characterization of C, C -Type Palladacycles and Their Catalytic Application in Mizoroki-Heck Coupling Reaction
Lo, Chi Hou,Lee, Hon Man
, p. 1150 - 1159 (2018/04/17)
Two series of ligand precursors, based on imidazo[1,2-a]pyridine and C2-phenyl substituted imidazole moieties, were developed and synthesized in high yields, featuring an N-CH2(C=O)Ar substituent on the imidazole ring. Upon reacting with palladium acetate, both series of ligands underwent double C-H bond activations at the methylene and o-aryl carbon sites on the N-CH2(C=O)Ar substituent, yielding C,C-type palladacycles bearing five-membered chelate rings. A dimeric palladium complex with bridging bromides was obtained from the ligand precursor with the bromide anion, whereas an ionic palladium complex with two "throw away" pyridine ligands was formed with the precursor of the tetrafluoroborate anion. All complexes are air-stable and were characterized by 1H and 13C NMR spectroscopy and elemental analysis. The structures of three of the new complexes were further established by single-crystal X-ray diffraction studies. These complexes have been screened for catalyzing Mizoroki-Heck coupling reaction using ionic salt as solvent. The complex based on imidazo[1,2-a]pyridine, which has an electron-donating 4-methoxyphenyl ring on the ligand scaffold, was the most efficient catalyst, capable of using activated aryl chloride and sterically hindered aryl bromide as substrates. It was also successfully applied in the green process of one-pot Mizoroki-Heck coupling/trans-esterification reaction in molten ionic salt.
