142557-76-4Relevant academic research and scientific papers
Ionic Liquid-Based Microemulsions in Catalysis
Hejazifar, Mahtab,Earle, Martyn,Seddon, Kenneth R.,Weber, Stefan,Zirbs, Ronald,Bica, Katharina
, p. 12332 - 12339 (2016)
The design and properties of surface-active ionic liquids that are able to form stable microemulsions with heptane and water are presented, and their promise as reaction media for thermomorphic palladium-catalyzed cross-coupling reactions is demonstrated.
Palladium(II) complexes bearing N-alkylpiperidoimidazolin-2-ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity
?ak?r, Sinem,Türkmen, Gül?ah,Türkmen, Hayati
, (2018)
A series of piperidoimidazolinium salts which differ in the chain lengths (butyl, octyl, dodecyl, octadecyl) and their Pd–N-heterocyclic carbene complexes with pyridine were synthesized and characterized using elemental analysis and spectroscopic methods. The effects of these ligands on catalyst activation and the performance of the complexes were studied in Suzuki–Miyaura reactions of arylboronic acid with aryl chlorides. The complex with the ligand having the longest chain length was found to be most active. The results demonstrated that the length of the alkyl chain of the piperidoimidazolin-2-ylidene controlled the dispersion and composition of the nanoparticles and it affected the catalytic activity. The impact of alkyl chain length of piperidoimidazolin-2-ylidene on the Suzuki–Miyaura reactions of arylboronic acid with aryl halides was systematically investigated.
Iron-catalyzed Suzuki-Miyaura cross-coupling reaction
Bezier, David,Darcel, Christophe
, p. 1732 - 1736 (2009)
An efficient, mild, and simple protocol for iron-catalyzed Suzuki-Miyaura type cross-coupling reaction between iodo- or bromoaryl derivatives and arylboronic acids was developed. In the presence of iron(III) chloride (10 mol%) and a stoichiometric amount of potassium fluoride, aryl iodides and bromides reacted with arylboronic acids in ethanol at 100 °C under air to give the corresponding bis-aryl compounds with good to excellent yields.
Amine-bridged bis(phenol) ligands for efficient Pd-catalyzed aqueous C-C coupling reactions
Zhou, Zhonggao,Liu, Minyan,Wu, Xiaoli,Yu, Hongwei,Xu, Guohai,Xie, Yongrong
, p. 562 - 569 (2013)
The influence of ring size (5 or 6), chain length (1, 2 or 3) and bulkiness of N-aryl substituents in amine-bridged bis(phenol) ligands (1, 2, 3) on palladium-catalyzed aqueous C-C coupling reactions were revealed. The homocoupling of arylboronic acid can be completed in neat water with the aid of a catalytic amount of p-toluenesulfonyl chloride (TsCl) in a very short time under anaerobic or aerobic conditions. Interestingly, the same catalytic system was efficient for Suzuki-Miyaura reaction in aqueous acetone under aerobic conditions in the absence of TsCl. The crystal structures of ligand 1 and three unsymmetrical fluorine-substituted biaryl derivatives were also reported. Copyright
Synthesis of chiral imidazolium salts from a carbohydrate and their application in Pd-catalyzed Suzuki-Miyaura reaction
Zhou, Zhonggao,Qiu, Jiabin,Xie, Lifang,Du, Fan,Xu, Guohai,Xie, Yongrong,Ling, Qidan
, p. 1911 - 1918 (2014)
A series of chiral 1-(acetylated glucopyranosyl)-3-substituted-imidazolium salts [3-substitute = nbutyl (1a), 3-bromopropyl (1b), 2-chloromethyl benzyl (1c), and 4-chloromethyl benzyl (1d)] have been synthesized. Preliminary catalytic studies show that these imidazolinium salts are remarkably efficient in Pd-catalyzed Suzuki-Miyaura reaction. Functionalized aryl boronic acids reaction with aryl halides (including aryl iodides, aryl bromides and activated aryl chlorides) using environmentally friendly conditions (ethanol aqueous and ambient). The excellent isolate yields reveal that the bulky carbohydrate unit is promising for the construction of highly active transition-metal catalyst.
Immobilization of dipyridyl complex to magnetic nanoparticle via click chemistry as a recyclable catalyst for Suzuki cross-coupling reactions
Lv, Guanghua,Mai, Wenpeng,Jin, Rizhe,Gao, Lianxun
, p. 1418 - 1422 (2008)
A magnetic nanoparticle (MNP)-supported di(2-pyridyl)methanol palladium dichloride complex was prepared via click chemistry. The MNP-supported catalyst was evaluated in Suzuki coupling reaction in term of activity and recyclability in DMF. It was found to be highly efficient for Suzuki coupling reaction using aryl bromides as substrates and could be easily separated by an external magnet and reused in five consecutive runs without obvious loss of activity. Georg Thieme Verlag Stuttgart.
PEG-supported dipyridyl ligand for palladium-catalyzed Suzuki and Suzuki-type reactions in PEG and aqueous media
Mai, Wenpeng,Gao, Lianxun
, p. 2553 - 2558 (2006)
An air- and water-stable PEG-supported bidentate nitrogen ligand is prepared and its applications in the palladium-catalyzed Suzuki reaction of aryl halides with arylboronic acids in PEG and Suzuki-type reaction of aryl halides with sodium tetraphenylborate in aqueous media are reported. The homogeneous catalyst system is environmentally friendly and offers the advantages of high activity, reusability and easy separation. Georg Thieme Verlag Stuttgart.
PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water
Xue, Jun,Zhou, Zhonggao,Peng, Jie,Du, Fan,Xie, Lifang,Xu, Guohai,Huang, Guiping,Xie, Yongrong
, p. 221 - 224 (2014)
We have used poly(ethylene glycol)-functionalized N-heterocyclic carbene ligands, 1-(methoxy PEG)-3-methylimidazolium iodides together with Pd(OAc) 2 as efficient catalysts for the Suzuki reaction in water. The best catalytic system generated in situ from Pd(OAc)2, mPEG 16MeImI, and K2CO3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6 h. After extraction of the product, the catalyst containing mPEG n MeImI phase could be recycled for five times without significant loss of activity. Graphical Abstract: Three PEG-modified NHC ligands with different PEG chain lengths (mPEGnMeImI, n = 7, 12, and 16) were used for Pd-catalyzed Suzuki reactions in water. The best catalytic system generated in situ from Pd(OAc)2, mPEG16MeImI, and K 2CO3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6 h. After extraction of the product, the catalyst containing mPEGn MeImI phase could be recycled for five times without significant loss of activity.
New biomaterials for Ni biosorption turned into catalysts for Suzuki-Miyaura cross coupling of aryl iodides in green conditions
Cases, Lucie,Adler, Pauline,Pelissier, Franck,Diliberto, Sébastien,Boulanger, Clotilde,Grison, Claude
, p. 28085 - 28091 (2021/09/15)
In parallel with increasing Ni production and utilisation, Ni pollution in the soil-water continuum has become an alarming and global problem. Solutions for removing Ni from industrial effluents have been widely investigated and biosorption has emerged as an efficient, cost-effective, scalable and sustainable alternative for water treatment. However, the biosorption capacity is limited by the chemical composition of the biomaterial and the Ni-enriched biomaterials are rarely valorised. In this work, the biosorption capacity of three abundant biomaterials with different chemical properties - water hyacinth, coffee grounds and pinecones - was studied before and after functionalization, and reached a maximum biosorption capacity of 51 mg g?1of Ni(ii). A bioinspired functionalization approach was investigated introducing carboxylate moieties and was conducted in green conditions. The Ni-enriched biomaterials were valorised by transformation into catalysts, which were characterised by MP-AES and XRPD. Their characterisation revealed a structure similar to nickel formate, and hence the Eco-Ni(HCOO)2catalysts were tested in Suzuki-Miyaura reactions. Several aryl iodides were successfully cross-coupled to phenylboronic acids using Eco-Ni(HCOO)2without any ligand, a mild and green base in a mixture of green solvents.
Complexes LNi(Cp)X with alkylamino-substituted N-heterocyclic carbene ligands (L) and their catalytic activity in the Suzuki—Miyaura reaction
Chernyshev, V. M.,Chesnokov, V. V.,Shevchenko, M. A.,Soliev, S. B.,Tafeenko, V. A.
, p. 1281 - 1289 (2021/08/10)
New nickel(ii) complexes of the general formula LNi(Cp)X (L is an N-heterocyclic carbene (NHC) ligand of the 1,2,4-triazole or imidazole series; Cp is the cyclopentadienyl anion; X = Cl, I) are reported. In these complexes, the NHC ligands (L) contain an alkylamino group at the 3 or 4 position of the heterocycle. The synthesized complexes and structurally similar complexes without an alkylamino group were tested for catalytic activity in the Suzuki—Miyaura reaction. The introduction of an alkylamino group into the NHC ligand leads to the enhancement of the catalytic activity of complexes with N,N′-diaryl-substituted NHC ligands of the imidazole series and a decrease in the activity of the complexes with N,N′-dialkyl-substituted NHC ligands of the 1,2,4-triazole series.
