116868-96-3Relevant articles and documents
Microwave-promoted Heck coupling using ultralow metal catalyst concentrations
Arvela, Riina K.,Leadbeater, Nicholas E.
, p. 1786 - 1790 (2005)
(Chemical Equation Presented) We show that Heck couplings can be performed in water using microwave heating and Pd catalyst concentrations as low as 500 ppb. The methodology is simple; all that is required as the catalyst is a stock solution of palladium.
A silica-supported palladium-bis(oxazoline) complex efficiently catalyzes the synthesis of cinnamic acid derivatives via Mizoroki–Heck coupling reactions
Ibrahim, Mansur B.,Suleiman, Rami,Fettouhi, Mohammed,El Ali, Bassam
, p. 1 - 8 (2017)
A palladium(II)-bis(oxazoline) complex supported on silica (Pd-BOX-Si) was prepared, characterized and applied as a catalyst in Mizoroki–Heck cross-coupling reactions. The bis(oxazoline) (BOX) ligand has a hydroxyl group that can be anchored to 4-benzyl chloride-functionalized silica gel, followed by the coordination of palladium(II) chloride. The catalytic activity and the recyclability of Pd-BOX-Si have been investigated in the production of cinnamic acid derivatives via Mizoroki–Heck coupling reactions of acrylates with aryl halides; The Pd-BOX-Si catalyst demonstrated excellent catalytic activity. Characterization of the recycled Pd-BOX-Si catalyst revealed its good stability under the reaction conditions employed.
Polypyrrole-palladium nanocomposite-coated latex particles as a heterogeneous catalyst in water
Ohtaka, Atsushi,Kono, Yuki,Teratani, Takuto,Fujii, Syuji,Matsuzawa, Soichiro,Nakamura, Yoshinobu,Nomura, Ryoki
, p. 1097 - 1103 (2011)
Polypyrrole-palladium nanocomposite-coated cross-linked polystyrene latex particles (PS/PPy-Pd) showed an excellent catalytic activity for Suzuki and Heck reactions in aqueous media. The PS/PPy-Pd can be recovered easily and quantitatively through the repeated uses with simple filtration and they maintain their high catalytic activities.
Pd-catalyzed C#C cross-coupling reactions within a thermoresponsive and pH-responsive and chelating polymeric hydrogel
Wang, Yao,Zhang, Jianzheng,Zhang, Wangqing,Zhang, Minchao
, p. 1923 - 1931 (2009)
A porous, thermoresponsive and pH-responsive, and chelating hydrogel of poly(N-isopropylacrylamide)co-poly[2-methacrylic acid 3-(bis-carboxymethylamino) -2-hydroxypropyl ester] (PNIP AM-co-PMACHE) is proposed as both a reaction medium and the Pd catalyst support for organic synthesis. Organic synthesis within the PNIPAM-co-PMACHE hydrogel has three merits. First, organic reactions such as Suzuki and Heck reactions within the hydrogel can be accelerated due to the enriched Pd catalyst and reactants within the hydrogel by the reversible deswelling/swelling. Second, organic synthesis within the PNIPAM-co-PMACHE hydrogel, which holds about ～300 times of water and is similar to the environmentally benign reaction medium of water, can be performed efficiently without surfactant or cosolvent being added. Third, the PNIPAM-co-PMACHE hydrogel itself and the therein-immobilized Pd catalyst can be easily recycled since the hydrogel/Pd composite can reversibly swell/deswell.
Reusable, magnetic Raney nickel based palladium catalysts for the Heck coupling in aqueous media
Bumagin, N. A.
, p. 2034 - 2040 (2021/11/05)
Hybrid materials based on Pd- and Cu-doped Raney nickel appeared to be highly efficient catalysts for the Heck reaction in aqueous media in the absence of organic cosolvents. The catalysts can be easily removed by an external magnet and reused without losing catalytic activity.
Oxime-derived palladacycle Immobilized in an Ionic Liquid Brush as an Efficient and Reusable Catalyst for Mozoroki-Heck Reaction in Neat Water
Wang, Rong,Li, Shan,Li, Jing,Wei, Junfa
, (2019/09/17)
An efficient and reusable heterogeneous catalyst with oxime-derived palladacycle immobilized in an ionic liquid brush has been synthesized and an environmentally-friendly procedure have been developed for coupling aryl iodides and bromides with acrylic acid. These reactions were conducted in neat water under aerobic conditions with water-insoluble or even solid aryl halides and they proceeded smoothly and cleanly without any organic co-solvent or other additives. The ionic liquid brush could be easily recovered and reused at least five times without significant loss of activity. The protocol has the advantages of excellent yields, environmental friendliness, and catalyst recyclability.
Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: A direct photocatalytic approach to cinnamic acids
Tripathi, Shubhangi,Yadav, Lal Dhar S.
supporting information, p. 3765 - 3769 (2018/03/06)
The first workable application of β-nitrostyrenes and CBr4 as coupling partners for a highly stereoselective synthesis of (E)-cinnamic acids under visible light photoredox catalysis is reported. The reaction involves a radical denitrative tribromomethylation/hydrolysis cascade to afford (E)-cinnamic acids in excellent yields at room temperature in a one-pot procedure. Moreover, the implementation of visible light as a clean and inexpensive energy source and CBr4 as the latent source of carboxylic groups makes the protocol reconcilable with the present day scenario of organic synthesis.
An efficient Pd-NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki-Heck reactions in water
Sun, Nan,Chen, Meng,Jin, Liqun,Zhao, Wei,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
supporting information, p. 1735 - 1744 (2017/09/27)
Three PEG-functionalized imidazolium salts L1-L3 were designed and prepared from commercially available materials via a simple method. Their corresponding water soluble Pd-NHC catalysts, in situ generated from the imidazolium salts L1-L3 and Na2PdCl4 in water, showed impressive catalytic activity for aqueous Mizoroki-Heck reactions. The kinetic study revealed that the Pd catalyst derived from the imidazolium salt L1, bearing a pyridine-2-methyl substituent at the N3 atom of the imidazole ring, showed the best catalytic activity. Under the optimal conditions, a wide range of substituted alkenes were achieved in good to excellent yields from various aryl bromides and alkenes with the catalyst TON of up to 10,000.
Polystyrene supported palladium nanoparticles catalyzed cinnamic acid synthesis using maleic anhydride as a substitute for acrylic acid
Thakur, Vandna,Kumar, Sandeep,Das, Pralay
, p. 3692 - 3697 (2017/09/07)
Maleic anhydride was explored as a substitute for acrylic acid to synthesize cinnamic acids from aryl halides under heterogeneous palladium catalyzed conditions. The combined role of surface and impregnated catalyst together performed an upright engineering to hold in situ generated molecules on the surface and subsequently facilitate their interaction for the desired product synthesis. Overall, a surface mediated approach for cinnamic acid synthesis from maleic anhydride following a major unexplored pathway through catalyst promoted decarboxylation was critically investigated.
Magnetic polymer nanocomposite-supported Pd: An efficient and reusable catalyst for the Heck and Suzuki reactions in water
Wang, Dongfang,Liu, Wendong,Bian, Fengling,Yu, Wei
, p. 2052 - 2059 (2015/03/18)
A novel type of magnetically responsive polymer nanocomposite Fe3O4@poly(undecylenic acid-co-4-vinyl pyridine-co-sodium acrylate) (Fe3O4@PUVS) was synthesized by the free radical polymerization of 4-vinyl pyridine (4-VP) with sodium acrylate (SAA) and Fe3O4@undecylenic acid. Pd2+ was then immobilized on this magnetic nanocomposite to form the magnetic Fe3O4@PUVS-Pd catalyst. This catalyst exhibited excellent catalytic activity for the Heck and Suzuki coupling reactions in water, and could be simply separated by using a permanent magnet. The supported catalyst could be used consecutively for six runs without significant loss of catalytic activity.
