169479-49-6Relevant articles and documents
Highly efficient nickel-catalyzed Heck reaction using Ni(acac)2/ N-heterocyclic carbene catalyst
Inamoto, Kiyofumi,Kuroda, Jun-Ichi,Danjo, Tomohiro,Sakamoto, Takao
, p. 1624 - 1626 (2005)
Ni(acac)2/N-heterocyclic carbene-derived catalysts were shown to be highly efficient in the nickel-catalyzed Heck reaction. Various aryl halides were reacted with acrylate to give the coupled products in good to high yield. Georg Thieme Verlag
Palladium-containing ionic liquid-based ordered mesoporous organosilica: An efficient and reusable catalyst for the heck reaction
Elhamifar, Dawood,Karimi, Babak,Rastegar, Javad,Banakar, Mohammad Hossain
, p. 2418 - 2424 (2013)
The catalytic application of a novel palladium-containing periodic mesoporous organosilica with ionic liquid framework (Pd@PMO-IL-I) in the Heck cross-coupling reaction was described. This nanocatalyst was first synthesised and characterised by using diffuse reflectance infrared Fourier transform spectroscopy, thermogravimetric analysis, transmission electron microscopy and nitrogen sorption analysis. The efficiency of the Pd@PMO-IL-I catalyst was investigated in the Heck cross-coupling of various aryl halides with alkyl acrylates in the presence of N-methylpyrolidone at 140°C. The catalyst demonstrated excellent catalytic activity with various aryl iodides, aryl bromides, and activated aryl chlorides, which gave the corresponding coupling products in good to excellent yields and with excellent E-selectivities. Moreover, the recoverability, reusability and the actual nature of the Pd@PMO-IL-I catalyst were investigated to show the effect of ionic liquid moieties on the stabilisation of palladium species during the reaction. Our study showed that the catalyst could be recovered and reused at least nine times without any appreciable decrease in activity and selectivity, which confirmed its high efficiency and high stability under the reaction conditions and during recycling stages.
Synthesis of vinylated 5,10,15,20-tetraphenylporphyrins via heck-type coupling reaction and their photophysical properties
Pereira, Mariette M.,Muller, Guillermo,Ordinas, Juan Ignacio,Azenhaa, M. Emilia,Arnaut, Luis G.
, p. 1583 - 1588 (2002)
The direct coupling reaction between substituted olefins and 5,10,15,20-tetrakis(4-bromophenyl)porphyrin, via a Heck-type reaction, constitutes a versatile method for the vinylation of 5,10,15,20-tetrakis(4-bromophenyl)porphyrin to yield new vinylated tetraphenylporphyrins quantitatively. Another strategy for the vinylporphyrin synthesis has been developed. A phosphapalladacycle has been used as catalyst for the coupling reaction between 4-bromoaryl aldehydes and olefins to yield vinyl aldehydes quantitatively. These aldehydes have been condensed with pyrrole, by the one-step nitrobenzene method, to give the corresponding vinylated tetraphenylporphyrins. Photophysical studies of these new porphyrins are also reported.
Comprehensive kinetic screening of palladium catalysts for heck reactions
Blackmond, Donna G.,Schultz, Thomas,Mathew, Jinu S.,Loew, Caroline,Rosner, Thorsten,Pfaltz, Andreas
, p. 3135 - 3139 (2006)
Comprehensive kinetic screening of Pd catalysts for Heck reactions via a consecutive pulse reaction methodology allows a more informed choice of catalyst for a particular transformation, taking into account not only initial reactivity but also long-term c
Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides
Hung, Cheng-Hau,Zheng, Wei-Yuan,Lee, Hon Man
, p. 702 - 713 (2021/04/02)
Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.
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.
Efficient Mizoroki–Heck coupling reactions using phosphine-modified Pd(II)–picolinate complex
Sharma, Sonam,Sarkar, Bibhas R.
supporting information, p. 906 - 914 (2018/03/21)
Efficient Mizoroki–Heck couplings were obtained using a very easily synthesizable palladium(II) complex of hemilabile N–O ligand (picolinate), with high turnover frequencies up to >10,000 h?1, in just 15 min, with high selectivity of >99% to the desired products. Wide applicability of the simple-looking palladium complex catalyst was established with differently functionalized substrates. Catalyst screening studies revealed intricate details of dependence of catalyst performance on different reaction parameters and conditions and arriving at the optimized facile methodology.
