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2132-80-1

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2132-80-1 Usage

Chemical Properties

light yellow shiny flakes

Uses

4,4′-Dimethoxybiphenyl was used to study the coupled methyl-group rotation and methoxy-group libration.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 4780, 1972 DOI: 10.1021/ja00768a084Organic Syntheses, Coll. Vol. 6, p. 468, 1988Tetrahedron Letters, 13, p. 2271, 1972

Check Digit Verification of cas no

The CAS Registry Mumber 2132-80-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,3 and 2 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2132-80:
(6*2)+(5*1)+(4*3)+(3*2)+(2*8)+(1*0)=51
51 % 10 = 1
So 2132-80-1 is a valid CAS Registry Number.

2132-80-1Relevant articles and documents

Quinonediimines as redox-active organocatalysts for oxidative coupling of aryl- and alkenylmagnesium compounds under molecular oxygen

Amaya, Toru,Suzuki, Riyo,Hirao, Toshikazu

, p. 7790 - 7793 (2016)

It is revealed that N,N′-diphenyl-p-benzoquinonediimine works as a redox-active organocatalyst for the oxidative homo-coupling of aryl- and alkenylmagnesium compounds under molecular oxygen. The catalytic cycle was formally monitored by 1H NMR experiments.

Stable Fe(ii)-based coordination polymers: Synthesis, structural diversity and catalytic applications in homo-coupling reactions

Wu, Qiong,Han, Yanbing,Shao, Zhichao,Li, Junxia,Hou, Hongwei

, p. 8063 - 8069 (2018)

Herein, we synthesize three new stable Fe(ii) coordination polymers, {[Fe3(tttmb)4(OH)(NCS)5]2CH3OH·H2O}n (1), {[Fe3(tttmb)4(NCS)6]·3H2O}n (2), and {[Fe3(tttmb)2Cl6(H2O)6]·5H2O}n (3) (tttmb = 1,3,5-tris(triazole-1-ylmethyl)-2,4,6-trimethyl-benzene) under the regulation of KSCN and solvents and use them as green heterogeneous catalysts in aryl homo-coupling reactions. The catalytic experiments show that 1 and 3 exhibit high efficiency for aryl homo-coupling reactions under an air environment with a yield of up to 80%. Furthermore, the crystal structure analysis reveals that 1 and 3 have coordinated water molecules and OH-, which are easily removed from the host materials during the reactions. In contrast, no unsaturated coordination sites are generated in 2 during the reaction process. In addition, the variable temperature magnetic susceptibilities of 1-3 prove that the metal centers of these polymers are bivalent and all of them exhibit a weak antiferromagnetic effect.

A supramolecular peptide nanofiber templated Pd nanocatalyst for efficient Suzuki coupling reactions under aqueous conditions

Khalily, Mohammad Aref,Ustahuseyin, Oya,Garifullin, Ruslan,Genc, Rukan,Guler, Mustafa O.

, p. 11358 - 11360 (2012)

A bioinspired peptide amphiphile nanofiber template for formation of one-dimensional Pd nanostructures is demonstrated. The Pd and peptide nanocatalyst system enabled efficient catalytic activity in Suzuki coupling reactions in water at room temperature.

Palladium catalyzed the Suzuki cross-coupling reaction using a fluorous NHC ligand

Wan, Li,Yu, Hong,Cai, Chun

, p. 107 - 111 (2012)

The utilization of N-heterocyclic carbene palladium complex immobilized on fluorous silica gel through fluorous-fluorous interactions in the Suzuki cross-coupling reaction was described. The reactions were carried out under aerobic and phosphine-free conditions with moderate to excellent product yields. The catalyst was easily recovered and reused three times without significant loss of activity.

A new N–heterocyclic carbene palladium complex immobilized on nano silica: An efficient and recyclable catalyst for Suzuki–Miyaura [Formula presented] coupling reaction

Pahlevanneshan, Zari,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor–Baltork, Iraj,Loghmani-Khouzani, Hossein

, p. 31 - 37 (2016)

A new catalytic system based on Pd–NHC complex utilizing (4–pyridyl)bis(imidazolyl)methane as a bidentate NHC ligand supported on nano?silica is introduced. The catalyst was characterized by FT–IR spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy dispersive X–ray analysis, transmission electron microscopy and elemental analysis. This heterogeneous catalytic system exhibited excellent activity in the Suzuki–Miyaura coupling reaction of various aryl halides with phenylboronic acid, and was reusable several times without significant loss of its catalytic activity.

A series of new mixed-ligand complexes based on 3,6-bis(imidazol-1-yl)pyridazine: Syntheses, structures, and catalytic activities

Zhou, Sheng-Bin,Wang, Xin-Fang,Du, Ceng-Ceng,Wang, Duo-Zhi,Jia, Dianzeng

, p. 3124 - 3137 (2017)

Seven new mixed-ligand complexes based on L [L = 3,6-bis(imidazol-1-yl)pyridazine], namely, [Ni(L)2(SCN)2]n (1), [Cu5(L)(1,2-BDC)4(μ3-OH)2]n (2), {[Cu4(L)2(1,3-HBDC)(1,3-BDC)(μ3-OH)4]·ClO4·2.6H2O}n (3), {[Ni(L)(1,4-BDC)H2O]·0.25H2O}n (4), [Co(L)(1,3,5-H2BTC)2H2O]n (5), {[Cu2(L)(2,6-PYDC)2(H2O)2]·4.4H2O}n (6), and {[Co(L)(4,4′-OBA)]·3.725H2O}n (7) [1,2-benzenedicarboxylic acid (1,2-H2BDC), 1,3-benzenedicarboxylic acid (1,3-H2BDC), 1,4-benzenedicarboxylic acid (1,4-H2BDC), 1,3,5-benzenetricarboxylic acid (1,3,5-H3BTC), 2,6-pyridine dicarboxylic acid (2,6-H2PYDC), and 4,4′-oxydibenzoic acid (4,4′-H2OBA)], have been synthesized by solvothermal reactions. Complexes 1 and 2 possess a two-dimensional (2D) layered structure, and the 2D framework of complex 1 can be rationalized to be a four-connected {44·62} topological sql network, while 2 exhibits a similar topological network with pentanuclear [Cu5(μ3-OH)2(μ2-COO-)6]2+ secondary building units (SBUs). Complex 3 presents an 8-connected sqc3 3D framework based on a chair-shaped [Cu4(μ3-OH)4]4+ SBU with a Schl?fli symbol of {424·64}. Complex 4 displays a 3D framework with diamondoid topology, which includes L/Ni(ii)/L helical chains. Complex 5 features a 1D chain structure formed by L ligands. Complex 6 shows a dinuclear structure, which is arranged into a 1D supramolecular chain by hydrogen-bonding interactions. The 3D framework of 7 presents a 4-connected porous architecture with a Schl?fli symbol of {66}, the same as that of complex 4. The powder X-ray diffraction spectra, IR spectra, UV-vis absorption spectra and thermal stabilities of 1-7 have been investigated. Moreover, in the complex-catalyzed homocoupling reaction of 4-substituted aryl iodides, the catalytic activities of 1-7 have also been studied and discussed.

Di-t-butyl(ferrocenylmethyl)phosphine: Air-stability, structural characterization, coordination chemistry, and application to palladium-catalyzed cross-coupling reactions

Sliger, Michael D.,Broker, Grant A.,Griffin, Scott T.,Rogers, Robin D.,Shaughnessy, Kevin H.

, p. 1478 - 1486 (2005)

Di-t-butyl(ferrocenylmethyl)phosphine (1) has been isolated and structurally characterized. This ligand was found to be reasonably air stable as a solid and it has been shown to possess electron donating ability similar to that of tri-i-propylphosphine. A

Dinuclear Systems in the Efficient Nickel-Catalyzed Kumada-Tamao-Corriu Cross-Coupling of Aryl Halides

Matsubara, Kouki,Yamamoto, Hitomi,Miyazaki, Satoshi,Inatomi, Takahiro,Nonaka, Keita,Koga, Yuji,Yamada, Yuji,Veiros, Luis F.,Kirchner, Karl

, p. 255 - 265 (2017)

Highly active dinuclear nickel(I) complexes bearing bulky N-heterocyclic carbene ligands have been shown to be involved in the catalytic cycle of the Kumada-Tamao-Corriu cross-coupling reaction of aryl halides. The results of several stoichiometric reactions and kinetics experiments have revealed that monovalent and divalent dinickel species are the active species in the highly efficient, nickel-catalyzed, Kumada coupling reactions of aryl halides.

Highly nucleophilic dipropanolamine chelated boron reagents for aryl-transmetallation to iron complexes

Dunsford, Jay J.,Clark, Ewan R.,Ingleson, Michael J.

, p. 20577 - 20583 (2015)

New aryl- and heteroarylboronate esters chelated by dipropanolamine are synthesised directly from boronic acids. The corresponding anionic borates are readily accessible by deprotonation and demonstrate an increase in hydrocarbyl nucleophilicity in comparison to other common borates. The new borates proved competent for magnesium or zinc additive-free, direct boron-to-iron hydrocarbyl transmetallations with well-defined iron(ii) (pre)catalysts. The application of the new borate reagents in representative Csp2-Csp3 cross-coupling led to almost exclusive homocoupling unless coupling is performed in the presence of a zinc additive.

Imidazole and imidazoline derivatives as N-donor ligands for nickel-catalyzed kumada-tamao-corriu coupling

Iwamoto, Ryo,Hayashi, Masahiko

, p. 713 - 718 (2012)

Imidazole and imidazoline (dihydroimidazole) derivatives can serve as simple and efficient ligands for the nickel-catalyzed Kumada-Tamao-Corriu coupling reaction. Among the imidazole and imidazoline derivatives in our investigations, the 2-phenyllimidazoline-nickel (II) chloride complex exhibited the highest catalytic activity.

Palladium- and copper-catalyzed homocoupling of organolead compounds: Synthesis of biaryls and diynes

Kang, Suk-Ku,Shivkumar, Uma,Ahn, Chuljin,Choi, Sang-Chul,Kim, Jae-Sun

, p. 1893 - 1897 (1997)

The palladium- and copper-catalyzed dimerization of aryl- and alkynyllead triacetates to form biaryls and dialkynes under mild conditions is described.

Copper- and manganese-catalyzed homocoupling of organostannanes in the presence of iodine

Kang, Suk-Ku,Baik, Tae-Gon,Jiao, Xiang Hua,Lee, Yong-Tack

, p. 2383 - 2384 (1999)

The copper- and manganese-catalyzed homocoupling of aryl-, alkenyl-, and alkynylstannanes to afford biaryls, 1,3-dienes, and 1,3-diynes were achieved in the presence of iodine at 100 °C in good yields.

SYNTHESIS AND MASS SPECTROMETRY OF SOME METHOXYLATED PCB

Bergman, A.,Klasson Wehler, E.,Kuroki, H.,Nilsson, A.

, p. 1921 - 1938 (1995)

The syntheses of 46 methoxy-polychlorobiphenyls (MeO-CBs), containing 3 to 7 chlorine atoms, are described. The MeO-CBs were synthesized via the Cadogan diaryl coupling reaction of the appropriate polychloroaniline and polychloroanisole, or via the Ullmann coupling of a polychloroiodobenzene and 4-iodoanisole with subsequent chlorination of the isolated 4-MeO-CB product. The synthesized MeO-CBs were characterized by electron ionization (EI) mass spectrometry (MS) on an ion trap MS instrument and by EI and negative ion chemical ionization (NICI) on a quadrupole mass spectrometer. Both instruments gave similar EI spectra but the fragments were in general more abundant relative to the molecular ion, in the spectra obtained from the ion trap instrument. Characteristic fragmentation patterns were obtained by EI for ortho-, meta- and para-MeO-CBs, respectively, depending on the position of the MeO-group, with the exception of three meta-substituted MeO-heptaCBs, with a 3-MeO-2,4,6-trichloro-substitution pattern, that gave an abundant +-fragment, similar to para-substituted MeO-CBs. MS(NICI) of ortho-, meta- and para-MeO-CBs did not give any characteristic fragmentation patterns depending on the position of the MeO-group, except for ortho-substituted MeO-CBs that showed abundant fragments at -. The MS(NICI) gave approximately 10-50 times higher response for MeO-tetraCBs - MeO-heptaCBs than the MS(EI). The ion trap instrument (ITS40) has a somewhat lower detection-limit than the quadrupole MS when operated in the EI-mode.

Ullmann homocoupling catalysed by gold nanoparticles in water and ionic liquid

Monopoli, Antonio,Cotugno, Pietro,Palazzo, Gerardo,Ditaranto, Nicoletta,Mariano, Bruno,Cioffi, Nicola,Ciminale, Francesco,Naccia, Angelo

, p. 2777 - 2788 (2012)

The gold-catalysed Ullmann-type homocoupling of aryl halides is carried out with two different methodologies: (i) under micellar catalysis conditions in water and (ii) using a molten tetralkylammonium ionic liquid as the reaction medium. Glucose is used as a clean and renewable reductant. Morphology, size, and chemical composition of the gold nanoparticles were ascertained by X-ray photoelectron spectroscopy, transmission electron microscopy and dynamic light scattering analyses. A plausible reaction mechanism is proposed.

Captured and cross-linked palladium nanoparticles

Cho, Jin Ku,Najman, Romain,Dean, Tony W.,Ichihara, Osamu,Muller, Christophe,Bradley, Mark

, p. 6276 - 6277 (2006)

Polystyrene-poly(ethylene glycol) resin-captured cross-linked palladium nanopaticles were prepared via a straightforward route, and their heterogeneous behavior was truly confirmed by various tests. They were applied to aqueous Suzuki cross-coupling react

FeCl3 catalyzed barbier homocoupling reaction for synthesis of symmetric biaryls

Lee, Adam Shih-Yuan,Chen, Pin-Lung,Chang, Yu-Ting,Tsai, Heng-Tser

, p. 452 - 454 (2012)

Aseries of biaryls and biheteroaryls were synthesized by the Barbier reaction of aryl bromide withmagnesium powder and 1,2-dibromoethane in the presence of FeCl3 in THF under reflux reaction condition. The catalytic system differentiates itself fromother homocoupling reactions catalyzed by iron salts in that it requires neither the preliminary preparation of Grignard reagent nor the addition of an oxidant.

Rhodium/N-heterocyclic carbene-catalyzed cross-couplings of aryl arenesulfonates with arylboronic acids

Zhang, Liang,Wu, Jie

, p. 2409 - 2413 (2008)

The combination of rhodium(I) and N-hetercyclic carbenes (NHC) was found to be effective as a catalyst for cross-coupling reactions of aryl arenesulfonates with arylboronic acids, which gave rise to the desired biaryl compounds in good yields.

Sonogashira cross-coupling on the Au(1 1 1) and Au(1 0 0) facets of gold nanorod catalysts: Experimental and computational investigation

Lin, Jizhi,Abroshan, Hadi,Liu, Chao,Zhu, Manzhou,Li, Gao,Haruta, Masatake

, p. 354 - 361 (2015)

The catalytic activity of well-defined gold nanorods enclosed by Au(1 1 1) and Au(1 0 0) surfaces is investigated for the Sonogashira cross-coupling reaction between phenylacetylene and 4-iodoanisole, which gives rise to two homo-coupling products (diphen

An efficient catalyst for Suzuki-Miyaura coupling reaction in aqueous medium under aerobic conditions

Chen, Chuan-Lin,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung

, p. 521 - 523 (2005)

A cylcopalladated complex, [Pd(Cl)(k2N,C-CH2C 6H2(Me)2CHNC6H3(Pr i)2]2 was found to be an excellent catalyst for Suzuki-Miyaura coupling of aryl halides with arylboronic acid in aqueous medium under aerobic conditions.

Half-sandwich NHC-nickel(ii) complexes as pre-catalysts for the fast Suzuki coupling of aryl halides: A comparative study

Ritleng, Vincent,Oertel, Anna Magdalena,Chetcuti, Michael J.

, p. 8153 - 8160 (2010)

Cationic half-sandwich nickel complexes of general formula [Ni(NHC)(NCMe)(η5-C5R5)](PF6) [NHC = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) a, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) b; R = H, Me] were prepared from the reaction of their neutral homologues [Ni(NHC) Cl(η5-C5R5)] with 1 equiv. of KPF 6 in acetonitrile at room temperature. The new cationic complexes [Ni(IPr)(NCMe)(η5-C5Me5)](PF6) 3a, [Ni(IMes)(NCMe)(η5-C5Me5)](PF 6) 3b and [Ni(IMes)(NCMe)(η5-C5H 5)](PF6) 4b were obtained in high yield and were fully characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, elemental analyses, and in the case of 3a by a single-crystal X-ray diffraction study. The neutral analogue of 3a, [Ni(IPr) Cl(η5-C5Me5)] 1a was also structurally characterized. Their geometries were compared and no significant structural differences were observed. Nevertheless solution NMR spectroscopy established that the acetonitrile ligand of the cationic species is labile in solution. This results in the absence of any rotational significant barrier about the nickel-carbene carbon bond at ambient temperature in solution in the sterically congested cationic complexes 3a and 3b, in contrast to their neutral analogues 1a and [Ni(IMes)Cl(η5-C5Me5)] 1b. The neutral and the cationic complexes catalyzed the cross-coupling of phenylboronic acid with aryl halides in the absence of co-catalysts or reductants. Surprisingly, the neutral or cationic nature of the complexes proved to have almost no influence on the reaction yields and rates. However, complexes bearing the bulky electron-rich pentamethylcyclopentadienyl ligand were much more active than those bearing the cyclopentadienyl ligand, and TOF of up to 190 h-1, a high rate for nickel(ii) complexes under similar conditions, were observed with these species.

Suzuki–Miyaura cross-coupling reaction assisted by palladium nanoparticles-decorated zeolite 13X nanocomposite: a greener approach

Deepika, Raja,Sethuraman, Mathur Gopalakrishnan

, p. 1111 - 1128 (2022/01/22)

Heterogeneous catalysts govern the field of catalysis due to their easy separation from a reaction mixture, reusability, and prevention of agglomeration, making them more efficient catalysts than homogeneous catalysts. Herein, we report the eco-friendly synthesis of a novel heterogeneous catalyst, viz. palladium nanoparticles (Pd NPs) decorated over zeolite 13X nanocomposite using dried fruits of Terminalia chebula Retz. as the reducing and stabilizing agent and its performance as a promising catalyst for the Suzuki–Miyaura coupling reactions. The particle size, crystallinity, morphology, and textural properties of the catalyst were identified using Fourier transform-infrared spectroscopy (FTIR), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), high-resolution transmission electron microscopy (HR-TEM), thermal gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), and Brunauer–Emmett–Teller (BET) analysis which confirmed the presence of palladium nanoparticles on the surface of zeolite 13X. The FESEM images revealed the presence of spherical-shaped Pd NPs over the cubical particles of zeolite 13X. The average particle size of the palladium nanoparticles was found to be in the range of 6–7?nm and was polycrystalline in nature. From BET analysis, it was inferred that the decoration of Pd NPs decreased the surface area of zeolite 13X (615.5 m2/g to 548.334 m2/g), thus leaving pores unoccupied. This study showed the efficiency of this novel catalyst in the formation of biaryl derivatives using low palladium loadings (0.0012?mol%) giving good to excellent yields (90–99%) within short reaction times (10–225?min) with high TONs (> 79,000) and TOFs (> 21,000). Both electron-donating and electron-withdrawing aryl halides and aryl boronic acids reacted smoothly in the presence of K2CO3 as a base and EtOH/H2O (1:1) as the solvent. Besides, the catalyst could be recycled and reused for 5 consecutive runs with minimal loss of its efficiency. The supremacy of this catalyst could well be exploited in future for various organic transformations. Graphical abstract: [Figure not available: see fulltext.].

Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides

Albano, Gianluigi,Farinola, Gianluca M.,Giannini, Cinzia,Musio, Roberta,Omenetto, Fiorenzo G.,Rizzo, Giorgio,Sibillano, Teresa

supporting information, (2022/02/03)

Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex

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