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Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information
p. 6648 - 6653
(2021/09/08)

Silica-coated magnetic nanoparticles functionalized cobalt complex: a recyclable and efficient catalyst for the C?C bond formation
In this study, the Co-based catalyst was prepared by cobalt immobilization on the surface of functionalized silica-coated magnetic NPs (Fe3O4@SiO2-CT-Co) as a magnetically core–shell nanocatalyst and characterized by FT-IR, TGA, XRD, VSM, SEM, TEM, EDX, EDX mapping, and ICP techniques and appraised in the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions. The results displayed the superparamagnetic behavior of the Fe3O4 NPs core encapsulated by SiO2 shell, and the size of the particles was estimated about 30?nm. Compared with the previously reported catalysts, the engineered Fe3O4@SiO2-CT-Co catalyst provided perfect catalytic performance for the Suzuki–Miyaura cross-coupling reaction in water as a green solvent and it was much cheaper in the comparison with the traditional Pd-based catalysts. Importantly, the durability of magnetic nanocatalyst was studied and observed that it is stable under the reaction conditions and could be easily reused for at least six successive cycles without any significant decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.]
Haqjow, Hanif,Raoufi, Farveh
p. 4113 - 4128
(2021/07/26)

Microflowers formed by complexation-driven self-assembly between palladium(ii) and bis-theophyllines: Immortal catalyst for C-C cross-coupling reactions
The Pd catalyst for Suzuki-Miyaura or the other C-C coupling reactions is one of the central tools in organic synthesis related to medicine, agricultural chemicals and advanced materials. However, recycling palladium is a bottleneck for developing the extreme potential of Pd in chemistry. Herein, we established a new heterogeneous Pd catalytic system in which the catalyst is a nanopetal-gathered flower-like microsphere self-assembled from PdCl2 and alkyl-linked bis-theophyllines. The microflowers catalyzed quantitatively the reaction of aryl bromides and phenylboronic acid in aqueous media at room temperature. It was found that the reaction proceeds better in an air atmosphere than in nitrogen gas even though the Pd(ii) species employed was lowered to 0.001 mol% in the substance. Very interestingly, the microflowers could be recycled 20 times without deactivation in the C-C coupling reaction between bromobenzene and phenylboronic acid in the presence of sodium chloride. We found that the sodium chloride added played an important role in maintaining the morphology of microflowers and preventing the formation of metallic Pd particles.
Jin, Ren-Hua,Jou, Naoki,Kaikake, Katsuya,Shitara, Go
p. 35311 - 35320
(2021/11/30)

Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- And N-Chlorosuccinimide as Bifunctional Reagents
Exploration of alternative energy sources for chemical transformations has gained significant interest from chemists, and mechanochemistry is one of those sources. Herein, we report the use of N-bromosuccinimides (NBS) and N-chlorosuccinimides (NCS) as bifunctional reagents for a cascaded C-N bond formation and subsequent halogenation reactions. Under the solvent-free mechanochemical (ball-milling) conditions, the synthesis of a wide range of phenanthridinone derivatives from N-methoxy-[1,1′-biphenyl]-2-carboxamides is accomplished. During the reactions, NBS and NCS first assisted the oxidative C-N coupling reaction and subsequently promoted a halogenation reaction. Thus, the role of NBS and NCS was established to be bifunctional. Overall, a mild, solvent-free, convenient, one-pot, and direct synthesis of various bromo- and chloro-substituted phenanthridinone derivatives was achieved.
Bera, Shyamal Kanti,Mal, Prasenjit
p. 14144 - 14159
(2021/09/13)

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water
Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.
Abe, Manabu,Akita, Munetaka,Chitose, Youhei,Hyodo, Yuki,Koike, Takashi,Takahashi, Keigo,Yoshizawa, Michito
(2021/10/21)

Magnetization of graphene oxide nanosheets using nickel magnetic nanoparticles as a novel support for the fabrication of copper as a practical, selective, and reusable nanocatalyst in C-C and C-O coupling reactions
Catalyst species are an important class of materials in chemistry, industry, medicine, and biotechnology. Moreover, waste recycling is an important process in green chemistry and is economically efficient. Herein, magnetic graphene oxide was synthesized using nickel magnetic nanoparticles and further applied as a novel support for the fabrication of a copper catalyst. The catalytic activity of supported copper on magnetic graphene oxide (Cu-ninhydrin@GO-Ni MNPs) was investigated as a selective, practical, and reusable nanocatalyst in the synthesis of diaryl ethers and biphenyls. Some of the obtained products were identified by NMR spectroscopy. This nanocatalyst has been characterized by atomic absorption spectroscopy (AAS), scanning electron microscopy (SEM), wavelength dispersive X-ray spectroscopy (WDX), energy-dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), and vibrating sample magnetometer (VSM) techniques. The results obtained from SEM shown that this catalyst has a nanosheet structure. Also, XRD and FT-IR analysis show that the structure of graphene oxide and nickel magnetic nanoparticles is stable during the modification of the nanoparticles and synthesis of the catalyst. The VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, it can be reused several times without a significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst during organic reactions was confirmed by the hot filtration test and AAS technique.
Hajjami, Maryam,Moradi, Parisa
p. 25867 - 25879
(2021/08/09)

Preparation method of acrylamido
The present invention relates to a method for preparing a pyrimidine, 9-fluorenone as raw material, by open loop, acid chloride, amidation, chlorination, Hofmann (Hofmann) rearrangement degradation to give 2-(4'-chlorophenyl) aniline, and then condensed with 2-chloronicotinamide to give the product acetoimide, the present invention also relates accordingly to the intermediates 4'-chloro-2-bibenzamide and 4'-chloro-2-aminobiphenyl preparation method. The method of the present invention can obtain the target product with high yield, high purity, and can reduce costs while reducing environmental harm.
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Paragraph 0118; 0129-0134

(2022/01/04)

Palladium(II) complexes comprising naphthylamine and biphenylamine based Schiff base ligands: Synthesis, structure and catalytic activity in Suzuki coupling reactions
New palladium(II) Schiff base complexes of the general formula [Pd(L1?6)2] [L1 = N-(Naphthyl)-salicylaldimine (1), L2 = N-(Naphthyl)-methoxysalicylaldimine (2), L3 = N-(Biphenyl)-salicylaldimine (3), L4 = N-(Biphenyl)-methoxysalicylaldimine (4), L5 = N-(Naphthyl)-2-hydroxy-1-naphthaldimine (5), L6 = N-(Biphenyl)-2-hydroxy-1-naphthaldimine (6)] 1–6 have been synthesized by the reaction of [Pd(OAc)2] with bidentate Schiff base ligands. The palladium(II) complexes were fully characterized by analytical, spectral (FT?IR, UV–Vis, 1H NMR & 13C NMR) methods. The molecular structure of the one of the complexes [Pd(L1)2] (6) was confirmed by single crystal X?ray diffraction methods. Further, the new palladium(II) complexes were tested as catalyst for Suzuki-Miyaura coupling reactions and exhibits very good catalytic activity.
Balasubramani, Kasturi,Kaleeswaran, Dhananjayan,Nagalakshmi, Veerasamy,Premkumar, Muniyappan,Sathya, Munusamy,Venkatachalam, Galmari
(2020/03/18)

Remote and Selective C(sp2)-H Olefination for Sequential Regioselective Linkage of Phenanthrenes
Biphenylcarboxylic acid with two competing C(sp2)-H sites was designed for site selective C(sp2)-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.
Wei, Yi,Duan, Abing,Tang, Pan-Ting,Li, Jia-Wei,Peng, Rou-Ming,Zhou, Zheng-Xin,Luo, Xiao-Peng,Kurmoo, Mohamedally,Liu, Yue-Jin,Zeng, Ming-Hua
supporting information
p. 4129 - 4134
(2020/06/08)

Synthesis of seven-membered lactones by regioselective and stereoselective iodolactonization of electron-deficient olefins
A regio- A nd stereoselective iodolactonization of internal electron-deficient olefinic acids has been reported, which provides a straightforward access to a series of multi-functionalized seven-membered lactones containing two consecutive chiral centers. The ester substituents on the olefins played a key role in achieving high regioselectivity. This result was proved through experiments and DFT calculations.
Ke, Zhuofeng,Li, Ming,Liu, Yue-Jin,Luo, Xiao-Peng,Shao, You-Xiang,Tang, Pan-Ting,Wang, Liang-Neng,Wei, Yi,Zeng, Ming-Hua,Zhang, Ni-Juan
supporting information
p. 6680 - 6683
(2020/07/03)

Visible-Light-Induced Arene C(sp 2)-H Lactonization Promoted by DDQ and tert -Butyl Nitrite
A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp 2)-H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert -butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.
Chen, Bajin,Hu, Baoxiang,Hu, Xinquan,Jin, Liqun,Li, Meichao,Shen, Zhenlu,Sun, Nan,Wang, Shengpeng,Wang, Yiqing
supporting information
p. 261 - 266
(2020/02/18)

Controlled Synthesis of Palladium Nanocubes as an Efficient Nanocatalyst for Suzuki-Miyaura Cross-Coupling and Reduction of p-Nitrophenol
Anisotropic nanocatalysts have attracted considerable attention in comparison to bulk/nanocatalysts for their enhanced activity and reactivity. The demand toward anisotropic palladium (Pd) nanostructures has increased rapidly in the field of catalysis. Pd is a well-known active catalyst for several carbon-carbon (C-C) cross-coupling reactions; among them, the Suzuki-Miyaura cross-coupling reaction is one of the most versatile and dominant methods for constructing the extraordinarily useful unsymmetrical biaryls and also for hydrogenation of organic contaminants like p-nitrophenol (p-NP). This paper provides a brief explanation about the controlled synthesis, characterization, and catalytic activity of well-defined palladium nanocubes (Pd NCs) prepared by a seed-mediated method. The synthesized monodispersed Pd NCs were characterized by spectroscopic and microscopic tools such as UV-visible, XRD, FESEM, HRTEM, and EDS analyses. Pd NCs proved as an efficient catalyst for Suzuki-Miyaura cross-coupling reactions and p-NP reduction. The catalyst shows enhanced activity, greater stability, and higher selectivity with remarkable recyclability up to 92% for five consecutive cycles. The catalytic performance of the synthesized Pd NCs was also studied in the reduction of the organic contaminant p-NP, which showed an excellent performance screening of 99% conversion in 6 min.
Bhavya, M.,Bhol, Prangya,Kandathil, Vishal,Patil, Siddappa A.,Samal, Akshaya K.,Swain, Swarnalata
p. 5208 - 5218
(2020/06/10)

Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross-Coupling Reactions
Silk fibroin supported Pd (Pd/SF) has been prepared and used as catalyst in Suzuki–Miyaura cross-coupling reactions in water/ethanol (4:1 v/v) mixture. The reactions proceed rapidly with aryl iodides and boronic acids with different electronic properties using low metal loading (0.38 mol-%). Pd/SF exhibits better recyclability compared to other biopolymer-supported Pd catalysts, up to nineteen cycles without loss of activity.
Albano, Gianluigi,Farinola, Gianluca M.,Lo Presti, Marco,Milella, Antonella,Omenetto, Fiorenzo G.,Rizzo, Giorgio
supporting information
p. 6992 - 6996
(2020/11/30)

Synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline
The invention discloses a synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline, and belongs to the technical field of pesticide intermediate synthesis. The 2-(4 '-chlorphenyl) anilineis prepared by taking 9-fluorenone as an initial raw material through ring opening, chlorination, acylating chlorination, ammonification and Hofmann degradation reaction. The preparation method avoids the use of an expensive metal catalyst, the initial raw material is cheap and easy to obtain, and the method has the characteristics of simple reaction operation and high yield, and has higher valuein industrial production.
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Paragraph 0048-0054

(2020/09/23)

A self-assembling NHC-PD-loaded calixarene as a potent catalyst for the Suzuki-Miyaura cross-coupling reaction in water
Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 40-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.
Abdellah, Ibrahim,Couvreur, Patrick,Desma?le, Didier,Huc, Vincent,Martini, Cyril,Mougin, Julie,Pecnard, Shannon,Peramo, Arnaud
(2020/04/10)

NHC-Pd complex heterogenized on graphene oxide for cross-coupling reactions and supercapacitor applications
N-heterocyclic carbene (NHC)-palladium(II) complex (GO@NHC-Pd) was synthesized on graphene oxide (GO) support via a simple and cost-effective multistep approach. The spectroscopic, microscopic, thermal, and surface analyses of GO@NHC-Pd confirmed the successful formation of the catalyst. The investigation of catalytic activity showed that GO@NHC-Pd was very effective in Suzuki–Miyaura as well as Hiyama cross-coupling. Being heterogeneous in nature, GO@NHC-Pd was recovered after each reaction cycle easily and reused for up to nine and six cycles in Suzuki–Miyaura and Hiyama cross-coupling, respectively, without significant loss of activity. Further exploration of the supercapacitor performance of GO@NHC-Pd catalyst assembled in a two-electrode cell configuration shown a maximum attained capacitance of 105.26 F/g at a current density of 0.1 A/g with good cycling stability of 96.89% over 2,500 cycles.
Kandathil, Vishal,Siddiqa, Aisha,Patra, Abhinandan,Kulkarni, Bhakti,Kempasiddaiah, Manjunatha,Sasidhar,Patil, Shivaputra A.,Rout, Chandra Sekhar,Patil, Siddappa A.
(2020/07/25)

Synthesis and Biological Activity of Novel Succinate Dehydrogenase Inhibitor Derivatives as Potent Fungicide Candidates
In searching for novel fungicidal leads, the novel bioactive succinate dehydrogenase inhibitor (SDHI) derivatives were designed and synthesized by the inversion of carbonyl and amide groups. Bioassay indicated that compound 5i stood out with a broad spectrum of in vitro activity against five fungi. Its EC50 value (0.73 μg/mL) was comparable to that of boscalid (EC50 of 0.51 μg/mL) and fluxapyroxad (EC50 of 0.19 μg/mL) against Sclerotinia sclerotiorum. For Rhizoctonia cerealis, 5i and 5p with EC50 values of 4.61 and 6.48 μg/mL, respectively, showed significantly higher activity than fluxapyroxad with the EC50 value of 16.99 μg/mL. In vivo fungicidal activity of 5i exhibited an excellent inhibitory rate (100%) against Puccinia sorghi at 50 μg/mL, while the positive control boscalid showed only a 70% inhibitory rate. Moreover, 5i showed promising fungicidal activity with a 60% inhibitory rate against Rhizoctonia solani at 1 μg/mL, which was better than that of boscalid (30%). Compound 5i possessed better in vivo efficacy against P. sorghi and R. solani than boscalid. Molecular docking showed that even the carbonyl oxygen atom of 5i was far from the pyrazole ring. It could also form hydrogen bonds toward the hydroxyl hydrogen and amino hydrogen of TYR58 and TRP173 on SDH, respectively, which consisted of the positive control fluxapyroxad. Fluorescence quenching analysis and SDH enzymatic inhibition studies also validated its mode of action. Our studies showed that 5i was worthy of further investigation as a promising fungicide candidate.
Yang, Dongyan,Zhao, Bin,Fan, Zhijin,Yu, Bin,Zhang, Nailou,Li, Zhengming,Zhu, Yilin,Zhou, Jinghui,Kalinina, Tatiana A.,Glukhareva, Tatiana V.
p. 13185 - 13194
(2019/12/02)

From agriculture residue to catalyst support; A green and sustainable cellulose-based dip catalyst for C–C coupling and direct arylation
The core characteristics of a perfect catalyst include good activity, simple design, excellent stability, easy recovery from reaction mixture, recyclability, and have the provision for easy scale up. The ease in synthesis, recyclability and scale up makes the dip catalyst a major contender in this regard which possess most of the aforementioned characteristics. In this work, we report a dip catalyst made of cellulose, isolated from agriculture residue (sugarcane bagasse), in which biogenically synthesized palladium nanoparticles were dispersed. The prepared dip catalyst was characterized by FESEM, EDS, XRD, ATR-IR, TGA, TEM, XPS and ICP-OES analysis. Also, the activity of the dip catalyst was studied in the Suzuki-Miyaura cross-coupling reaction and was found to give excellent conversion with 15 recycles. Further, the activity of dip catalyst in C5-arylation of 2-substituted thiophenes was evaluated for which promising yields were obtained.
Kandathil, Vishal,Kempasiddaiah, Manjunatha,B. S., Sasidhar,Patil, Siddappa A.
(2019/07/31)

Convenient and efficient Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions catalyzed by 1,3,4-trisubstituted-1,2,3-triazolium iodide and palladium salt systems
A series of 1,3,4-trisubstituted-1,2,3-triazolium iodide salts (4a–c) were synthesized via a three-step reaction sequence. Corresponding anilines (1a–c) were converted to azides (2a–c) which were then treated with phenylacetylene with “Click” chemistry to access 1,4-disubstituted-1,2,3-triazoles (3a–c). Subsequent methylation of 1,4-disubstituted-1,2,3-triazoles (3a–c) yielded 1,3,4-trisubstituted-1,2,3-triazoliumiodide salts (4a–c) in appreciable yields. All the synthesized compounds were characterized by 1H and 13C NMR, ATR–IR spectroscopic techniques and elemental analyses. Additionally, the structure of 1-(4-chlorophenyl)-4-phenyl-1,2,3-triazole (3b) was confirmed by single crystal X-ray diffraction analysis. The catalytic activity of 4a–c in a catalytic system consisting of 1,3,4-trisubstituted-1,2,3-triazoliumiodide salt/palladium(II) acetate/base were investigated toward Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. The Suzuki–Miyaura cross-coupling reactions were carried out under mild reaction conditions with good to excellent yields, whereas Heck–Mizoroki cross-coupling reactions were performed at elevated temperature with moderate yields. Further, in situ method skips the synthetic procedure of preparing the palladium(II) complexes and hence is more economical and less tedious. (Figure presented.).
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Dateer, Ramesh B.,Müller-Bunz, Helge,Tacke, Matthias,Patil, Siddappa A.
p. 528 - 549
(2019/02/26)

Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D-HPLC
Amino acid derivatives undergo non-Kolbe electrolysis to afford enantiomerically enriched α-alkoxyamino derivatives through intermediate chiral carbenium ions. The products contain N,O-acetals which are important structural motifs found in bioactive natural products. The reaction is performed in a continuous flow electrochemical reactor coupled to a 2D-HPLC for immediate online analysis. This allowed a fast screening of temperature, electrode material, current, flow-rate and concentration in a DoE approach. The combination with online HPLC demonstrates that also stereoselective reactions can benefit from a hugely accelerated optimisation by combining flow electrochemistry with multidimensional analysis.
Ahmed, Nisar,Cicala, Rossana,Hardwick, Tomas,Santi, Micol,Seitz, Jakob,Wirth, Thomas
supporting information
p. 16230 - 16235
(2019/11/28)

Synthesis process of 2-(4-chlorophenyl)aniline
The invention discloses a synthesis process of 2-(4-chlorophenyl)aniline. The process adopts 9-fluorenone as a raw material, and uses four steps of ring opening, chlorination, amide amination and rearrangement degradation to obtain 2-(4-chlorophenyl) aniline. The process avoids the use of expensive raw materials and catalysts, and greatly reduces production costs. The content of the 2-(4-chlorophenyl)aniline prepared by the synthesis process is over 98%, and the total yield is over 75%.
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Paragraph 0016-0021

(2019/10/02)

Nickel-catalyzed carboxylation of aryl and heteroaryl fluorosulfates using carbon dioxide
The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.
Ma, Cong,Zhao, Chuan-Qi,Xu, Xue-Tao,Li, Zhao-Ming,Wang, Xiang-Yang,Zhang, Kun,Mei, Tian-Sheng
p. 2464 - 2467
(2019/04/10)

Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.
Bhunia, Samir Kumar,Das, Pritha,Nandi, Shantanu,Jana, Ranjan
supporting information
p. 4632 - 4637
(2019/06/27)

Synthesis, characterization and first application of covalently immobilized nickel-porphyrin on graphene oxide for Suzuki cross-coupling reaction
In this study, nickel(ii)-coordinated 5,10,15,20-tetrakis(aminophenyl)porphyrin (NiTAPP) as a macrocyclic complex was covalently grafted to the edge of graphene oxide (GO). The prepared nanocatalyst was well characterized by various techniques such as FT-IR, Raman, XRD, TEM, SEM, EDX, TGA, ICP-OES, UV and XPS. All analyses confirmed the successful immobilization of NiTAPP on GO. The synthesized catalyst was applied to evaluate its performance in the Suzuki-Miyaura cross-coupling reaction. GO/NiTAPP exhibited good catalytic efficiency with a high yield of products. Moreover, the suggested catalyst could be recycled for five consecutive cycles without a noticeable decrease in its catalytic activity or metal leaching.
Keyhaniyan, Mahdi,Shiri, Ali,Eshghi, Hossein,Khojastehnezhad, Amir
p. 19433 - 19441
(2018/12/13)

Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C-H Bonds
A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.
Pi, Jing-Jing,Lu, Xiao-Yu,Liu, Jing-Hui,Lu, Xi,Xiao, Bin,Fu, Yao,Guimond, Nicolas
p. 5791 - 5800
(2018/05/14)

Organometallic polymer-functionalized Fe3O4 nanoparticles as a highly efficient and eco-friendly nanocatalyst for C–C bond formation
A magnetically recoverable biopolymer-based nanocatalyst was prepared through the covalent immobilization of a chitosan-bound 2-hydroxynaphthaldehyde Pd complex on the surface of superparamagnetic nanoparticles. The nanocatalyst was characterized by FTIR, X-ray powder diffraction and scanning electron microscopy, revealing an average particle size of 70?nm. The catalyst shows high thermostability by thermogravimetric analysis. Estimated Pd loading by inductively coupled plasma atomic emission analysis was found to be 0.348?mmol?g?1. The nanocatalyst exhibits excellent catalytic performance in Suzuki couplings of various aryl halides with phenylboronic acid, and Heck reactions of iodo- and bromoarenes with butylacrylate. The catalyst can be easily separated from the reaction mixture with an external magnet and reused consecutively four times without significant loss in activity.
Fakhri, Akram,Naghipour, Ali
p. 463 - 472
(2018/04/17)

Ligand-Free Bioinspired Suzuki–Miyaura Coupling Reactions using Aryltrifluoroborates as Effective Partners in Deep Eutectic Solvents
Pd-catalyzed Suzuki–Miyaura cross-coupling between (hetero)aryl halides (Cl, Br, I) and versatile, moisture-stable mono- and bifunctional potassium aryltrifluoroborates proceeded efficiently and chemoselectively in air and under generally mild conditions; a catalyst loading as low as 1 mol % combined with Na2CO3 as a base in choline chloride/glycerol (1:2) deep eutectic solvent (DES) was used as a sustainable and environmentally responsible medium. The catalyst, base, and DES were easily and successfully recycled up to six times with an E-factor as low as 8.74. Valuable biaryls and terphenyl derivatives were furnished in yields of up to 98 %; over 50 reactions were compared and discussed. The methodology was applied for the synthesis of the nonsteroidal anti-inflammatory drugs Felbinac and Diflunisal.
Dilauro, Giuseppe,García, Sergio Mata,Tagarelli, Donato,Vitale, Paola,Perna, Filippo M.,Capriati, Vito
p. 3495 - 3501
(2018/09/21)

Polymer supported palladium complex as a reusable catalyst for Suzuki coupling
Novel, simple and efficient catalytic system based on a polymer supported Pd complex of 2,6-bis(benzimidazolyl)pyridine, Pd(PS–BBP)Cl2, was found to be highly active for Suzuki–Miyaura cross-coupling of aryl halides with phenylboronic acids under mild conditions. The catalyst was characterized by CHN analyses, thermogravimetric analyses, BET surface area measurements, ICP-OES, FT-IR and electronic spectral studies. The effect of solvent, base, temperature and catalyst concentration on the coupling reaction of iodobenzene with phenylboronic acid was also investigated. A variety of functional groups are tolerated. The novel catalyst could be recovered in a facile manner from the reaction mixture and could be reused up to seven times without significant loss of catalytic activity.
Renuka,Gayathri
p. 26 - 31
(2018/08/24)

Green Synthesis of Palladium Nanoparticles: Applications in Aryl Halide Cyanation and Hiyama Cross-Coupling Reaction Under Ligand Free Conditions
Abstract: In the current work, palladium nanoparticles (Pd NPs) were prepared from palladium acetate biogenically using the aqueous-ethanolic extract of black pepper (Piper nigrum) and characterized by various analytical techniques like XRD, FE-SEM, EDS, TEM, ATR-IR, UV–Vis spectroscopy, BET, TGA and ICP-OES analysis. The reduction of Pd(II)?to?Pd(0) is achieved by the action of various phytochemicals present in the black pepper extract like phenols, acids, pellitorine, ethyl piperonyl cyanoacetate, piperine and N-isobutyl-tetradeca-2,4-dienamide. The biosynthesized Pd NPs shown excellent catalytic activity in aryl halide cyanation and Hiyama cross-coupling reactions. Also, less toxic potassium hexacyanoferrate(II) trihydrate was used as cyanide source in aryl halide cyanation and Hiyama cross-coupling was performed under fluoride free condition. Both reactions proceeded well with Pd NPs under ligand free circumstances to give good to excellent yields. The Pd NPs were recovered after each reaction and recycled up to five times in aryl halide cyanation and ten times in Hiyama cross-coupling without considerable loss in the activity. Graphical Abstract: Green synthesis of palladium nanoparticles: applications in aryl halide cyanation and Hiyama cross-coupling reaction under ligand free conditions. [Figure not available: see fulltext.].
Kandathil, Vishal,Dateer, Ramesh B.,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.
p. 1562 - 1578
(2018/04/02)

Highly Dispersed Palladium Nanoparticle-Loaded Magnetic Catalyst (FeS@EP–AG–Pd) for Suzuki Reaction in Water
Abstract: In this work, an efficient epichlorohydrin–aminoguanidine-modified Fe3O4@SiO2 magnetic nanoparticles (FeS@EP–AG–Pd) with highly dispersed Palladium nanoparticles (Pd NPs) was reported for Suzuki reaction in water. After preparation of Fe3O4@SiO2 (FeS), special epichlorohydrin–aminoguanidine linker as a ligand with high content of heteroatoms was covalently bonded onto the FeS MNPs to increase their electron density. PdII ions were then loaded on surface of FeS@EP–AG MNPs and reduced for achieving the uniformly dispersed Pd NPs. FeS@EP–AG–Pd MNPs were performed in Suzuki reaction as an efficient catalyst in water as a green non-toxic solvent. Magnetically separable and recyclable FeS@EP–AG–Pd MNPs were then fully characterized by FTIR, SEM, TEM, TGA, VSM, XRD, and ICP–OES. The heterogeneous catalyst could also easily be recovered and reused with no loss of activity over 6 cycles. Graphical Abstract: [Figure not available: see fulltext.].
Sarvi, Iraj,Gholizadeh, Mostafa,Izadyar, Mohammad
p. 1162 - 1171
(2017/05/12)

Highly dispersed copper/ppm palladium nanoparticles as novel magnetically recoverable catalyst for Suzuki reaction under aqueous conditions at room temperature
An efficient procedure based on arginine-modified Fe3O4@carbon magnetic nanoparticles (FCA MNPs) with highly dispersed copper nanoparticles (Cu NPs) and 92.8?ppm of Pd is reported for room temperature Suzuki reaction. For enhancing the activity of this Cu-based heterogeneous catalyst, special arginine amino acid as a ligand with high content of heteroatoms was immobilized onto the Fe3O4@carbon MNPs to increase the electron density. Cu(II) ions were then loaded on the surface of the FCA MNPs and reduced to achieve uniformly dispersed Cu NPs. An aqueous mixture of metal hydroxides such as KOH, Ba(OH)2, Ca(OH)2, Mg(OH)2 as a green, non-toxic and basic medium was used for the Suzuki reaction at room temperature. This catalyst could also be recovered and reused with no loss of activity over six successful runs.
Lamei, Kamran,Eshghi, Hossein,Bakavoli, Mehdi,Rostamnia, Sadegh
(2017/09/30)

Carbon coated copper nanostructures as a green and ligand free nanocatalyst for Suzuki cross-coupling reaction
In this work, carbon coated copper nanoparticles and nanowires were synthesized as a ligand free nanocatalyst that naturally contains ppm levels of Pd with no post-modification via a two-steps reduction-hydrothermal process. Transmittance electron microscope (TEM), scanning electron microscope (SEM), X-ray diffraction, inductively coupled plasma optical emission spectrometry (ICP-OES), and Raman spectroscopy were employed for the characterization of the nano-catalyst. The utilization of the synthesized Cu/C nano-catalyst in Suzuki cross coupling reaction showed a high performance in the synthesis of various biaryls in water. Moreover, this catalyst reused successfully with no significant yield decrease even after four subsequently runs.
Lamei, Kamran,Eshghi, Hossein,Bakavoli, Mehdi,Rounaghi, Seyyed Amin,Esmaeili, Elaheh
p. 40 - 45
(2017/01/10)

Towards phosphine-free Pd(II) pincer complexes for catalyzing Suzuki-Miyaura cross-coupling reaction in aqueous medium
Pincer complexes can act as efficient catalysts for many industrially important organic transformations under environmentally benign and mild conditions. The NNN pincer ligands have been prepared from the reactions between pyridine-2,6-dicarbonyldichloride and benzylamine or its derivatives in the presence of 4-dimethylaminopyridine (DMAP). Pd(II) complexes containing NNN pincer ligand and acetonitrile/triphenylphosphine have been synthesized and characterized by analytical, spectroscopic (FT-IR, UV-Visible, 1H, 13C & 31P NMR and Mass) and single crystal X-ray diffraction techniques. Single crystal X-ray analysis reveals a distorted square planar geometry around Pd in all the complexes. These pincer complexes have been used as catalysts in Suzuki-Miyaura cross-coupling reaction. The effect of ancillary ligands (CH3CN and PPh3) in the complexes has been investigated towards the coupling reaction. The conversions have been determined from GC analyses. Scope of the system has been extended with various substituted halides.
Jerome, Peter,Sathishkumar, Pushpanathan N.,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
p. 115 - 124
(2017/07/22)

Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes
A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds.
Zhang, Jian,Shi, Dongdong,Zhang, Haifeng,Xu, Zheng,Bao, Hanyang,Jin, Hongwei,Liu, Yunkui
p. 154 - 163
(2016/12/23)

Palladium-Alumoxane Framework as a Novel and Reusable Nanocatalyst for Suzuki–Miyaura, Stille and Heck Cross Coupling Reactions
Abstract: Herein for the first time, a Schiff base alumoxane-supported palladium (SBA-Pd°) were successfully synthesized and reported as a new mesoporous nanocatalyst for C–C cross coupling reactions. The SBA-Pd° nanocatalyst could be dispersed in poly(ethylene glycol) and showed excellent catalytic activity for Suzuki–Miyaura, Stille and Heck coupling reactions. In addition, the nanocatalyst could be recovered and reused several times without significant loss of its catalytic activity. Pd leaching from SBA-Pd° is very negligible for this coupling reaction. Graphical Abstract: [Figure not available: see fulltext.]
Ghorbani-Choghamarani, Arash,Derakhshan, Ali Ashraf,Hajjami, Maryam,Rajabi, Laleh
p. 110 - 127
(2017/02/10)

Synthesis and Characterization of Pd Schiff Base Complex Immobilized onto Functionalized Nanoporous MCM-41 and its Catalytic Efficacy in the Suzuki, Heck and Stille Coupling Reactions
Abstract: The present work describes the use of palladium-vanillin-Schiff-base complex immobilized on MCM-41 nanostructure as efficient catalyst for the Suzuki–Miyaura, Stille and Mizoroki–Heck reactions of several aryl halides under aerobic conditions. All the reactions were carried out in green solvents (H2O and PEG-400). The developed procedure results bring several benefits such as uses of inexpensive and non-toxic ligand (vanillin), easy catalyst/product separation and catalyst recycling. The catalyst can be reused at least for five consecutive cycles without a significant loss of its catalytic activity or metal leaching. Graphical Abstract: [Figure not available: see fulltext.].
Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
p. 1114 - 1126
(2017/05/12)

Palladium supported on modified magnetic nanoparticles: A phosphine-free and heterogeneous catalyst for Suzuki and Stille reactions
An efficient magnetic nanoparticle-supported palladium (Fe3O4/SiO2-PAP-Pd) catalyst is reported for the Suzuki cross-coupling and Stille reactions. This method provides a novel and much improved modification of the Suzuki and Stille coupling reactions in terms of phosphine-free catalyst, short reaction time, clean reaction and small quantity of catalyst. Another important feature of this method is that the catalyst can be easily recovered from the reaction mixture and reused with no loss of its catalytic activity.
Ghorbani-Choghamarani, Arash,Norouzi, Masoomeh
p. 140 - 147
(2016/02/14)

Suzuki, Stille and Heck cross-coupling reactions catalyzed by Fe3O4@PTA-Pd as a recyclable and efficient nanocatalyst in green solvents
The use of a supported Pd complex on magnetic nanoparticles as an efficient and green catalyst for the Suzuki, Stille and Heck cross-coupling reactions is presented. The present research is focused on investigating the recycling, reusability and stability of the catalyst in the reaction. The recycled Fe3O4@PTA-Pd catalyst was used at least five times with comparable activities to that of the fresh catalyst. The catalytic coupling of 4-bromotoluene as a model reaction suggested that there was no leached palladium in the reaction mixture. The structure of the catalyst was characterized by TGA, EDS, ICP-OES, XRD, VSM, FT-IR and SEM analysis.
Ghorbani-Choghamarani, Arash,Norouzi, Masoomeh
p. 6299 - 6307
(2016/07/19)

Fe3O4@SiO2@ l -arginine@Pd(0): A new magnetically retrievable heterogeneous nanocatalyst with high efficiency for C-C bond formation
The surface of Fe3O4@SiO2 nanoparticles was modified using l-arginine as a green and available amino acid to trap palladium nanoparticles through a strong interaction between the metal nanoparticles and functional groups of the amino acid. The proposed green synthetic method takes advantage of nontoxic reagents through a simple procedure. Characterization of Fe3O4@SiO2@l-arginine@Pd(0) was done using Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and inductively coupled plasma analysis. The catalytic activity of Fe3O4@SiO2@l-arginine@Pd(0) as a new nanocatalyst was investigated in C-C coupling reactions. Waste-free, use of green medium, efficient synthesis leading to high yield of products, eco-friendly and economic catalyst, excellent reusability of the nanocatalyst and short reaction time are the main advantages of the method presented.
Ghorbani-Choghamarani, Arash,Azadi, Gouhar
p. 247 - 252
(2016/04/05)

Copper-Schiff base alumoxane: A new and reusable mesoporous nano catalyst for Suzuki-Miyaura and Stille C-C cross-coupling reactions
Herein for the first time, a mesoporous copper nano catalyst (SBA-Cu2+) were simply synthesized through immobilization of Cu2+ on surface of Schiff base alumoxane support. This nano catalyst was characterized by various techniques such as FT-IR, X-ray map, TG-DTA, BET, SEM, SEM-EDS, TEM, ICP-OES and XRD. The characterization results indicated that SBA-Cu2+ nanoflakes with 331.47 m2 g-1 specific surface area are thermally stable up to 306 °C. The SBA-Cu2+ nano catalysts showed significant activity for Suzuki-Miyaura and Stille cross-coupling reactions with good efficiency and reusability. In addition, the nanocatalyst could be recovered and reused several times without significant loss of its catalytic activity. Copper leaching from SBA-Cu2+ is very negligible for this coupling reaction.
Ghorbani-Choghamarani, Arash,Derakhshan, Ali Ashraf,Hajjami, Maryam,Rajabi, Laleh
p. 94314 - 94324
(2016/10/21)

Heterogeneous Fe3O4@chitosan-Schiff base Pd nanocatalyst: Fabrication, characterization and application as highly efficient and magnetically-recoverable catalyst for Suzuki-Miyaura and Heck-Mizoroki C-C coupling reactions
An environmentally friendly palladium-based catalyst supported on magnetite nanoparticles was successfully prepared. FT-IR, XRD, VSM, SEM, EDS and TGA studies have been used to characterize the nanocatalyst. The catalytic activity of the as-prepared catalyst was evaluated as a heterogeneous catalyst for the Suzuki-Miyaura carbon-carbon cross-coupling reaction of aryl halides and phenylboronic acid. Furthermore, it was found that the catalyst showed a high activity for the Mizoroki-Heck reaction of aryl halides and n-butyl acrylate. Interestingly, the novel catalyst could be recovered in a facile manner from the reaction mixture and recycled consecutive five runs without any significant loss in activity.
Naghipour,Fakhri
p. 39 - 45
(2015/10/28)

Application of Pd-2A3HP-MCM-41 to the Suzuki, Heck and Stille coupling reactions and synthesis of 5-substituted 1H-tetrazoles
An ecofriendly heterogeneous catalyst has been synthesized by anchoring palladium onto the surface of organically modified mesoporous silica. The prepared catalyst was characterized using X-ray diffraction, Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, inductively coupled plasma and thermogravimetric techniques. The catalyst shows high activity in the Suzuki, Heck and Stille cross-coupling reactions and the synthesis of 5-substituted 1H-tetrazoles from sodium azide (NaN3). These methods have the advantages of high yields, green reaction conditions, simple methodology and easy separation and workup.
Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Khanmoradi, Maryam
p. 705 - 712
(2016/07/19)

ortho-C?H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium
A system consisting of catalytic amounts of [(p-cym)RuCl2]2/PEt3?HBF4, K2CO3as the base, and NMP as the solvent efficiently mediates the ortho-C?H arylation of benzoic acids with aryl bromides at 100 °C. Replacing the phosphine ligand with the amino acid dl-pipecolinic acid enables the analogous transformation with aryl chlorides. The key advantage of this broadly applicable transformation is the use of an inexpensive ruthenium catalyst in combination with simple carboxylates as directing groups, which can either be tracelessly removed or used as anchor points for decarboxylative ipso substitutions.
Biafora, Agostino,Krause, Thilo,Hackenberger, Dagmar,Belitz, Florian,Goo?en, Lukas J.
supporting information
p. 14752 - 14755
(2016/11/23)

Uncatalyzed CO2Li-Mediated SNAr Reaction of Unprotected Benzoic Acids via Silicon Trickery
The alkyl and aryllithium nucleophilic aromatic substitution (SNAr) displacement of a fluoro or methoxy group from unprotected 2-fluoro/methoxybenzoic acids is discussed. It was discovered that a TMS group located at the C6-position ortho to the carboxyl group shields effectively the carboxylate against nucleophilic attack, thus reducing dramatically ketone formation, and reorients nucleophilic substitution to the C2-position. The reactions with fluoro-substituted substrate 7 proceed efficiently; in contrast, the use of methoxy-functionalized benzoic acid 8 only affords moderate yields with s-BuLi and PhLi. This uncatalyzed coupling reaction, which provides a direct access to biaryl compounds, presumably proceeds by an addition-elimination sequence via intermediate formation of a resonance-stabilized pentavalent silalactone-Meisenheimer complex.
Belaud-Rotureau, Mickael,Castanet, Anne-Sophie,Nguyen, Thi Huu,Mortier, Jacques
p. 307 - 313
(2016/03/30)

Room-temperature cobalt-catalyzed arylation of aromatic acids: overriding the ortho-selectivity via the oxidative assembly of carboxylate and aryl titanate reagents using oxygen
A room temperature phosphine or NHC ligand-free cobalt-catalyzed arylation of (hetero)aromatic acids has been developed. It involves an oxidative cross-coupling between carboxylate and aryl titanate reagents using oxygen as an oxidant, and the arylation at the position ortho, meta and para to the carboxylic acid group could all be achieved. As application, various (hetero)aromatic acids including xenalipin, tafamidis and the key intermediate for a cardioprotective compound have been efficiently synthesized.
Liu, Kun-Ming,Zhang, Rui,Duan, Xin-Fang
supporting information
p. 1593 - 1598
(2016/02/09)

Copper-Mediated ortho-Arylation of Benzamides with Arylboronic Acid
The copper-mediated direct ortho C-H bond arylation of benzamide derivatives with arylboronic acids was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various biaryls were synthesized in good yields with excellent regioselectivity. The reaction shows good functional group compatibility and proceeds in a highly selective manner at the ortho-position of the benzamides. Deuterium-labelling experiments indicated that the ortho C-H bond cleavage of benzamide was involved in the rate-determining step of the arylation.
Gui, Qingwen,Chen, Xiang,Hu, Liang,Wang, Dadian,Liu, Jidan,Tan, Ze
supporting information
p. 509 - 514
(2016/02/27)

Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids
A novel cobalt-promoted arylation of aryl C-H bonds with arylboronic acids has been realized by using 8-aminoquinoline as the directing group. The reaction tolerated a wide variety of functional groups and diversely substituted ortho-arylated benzamides were efficiently synthesized in good to excellent yields. Even though a catalytic amount of a Co-salt was enough to effect the transformation, better yields were obtained with a stoichiometric amount of the Co-salt. A notable feature of this newly developed protocol is that acrylamides, which cannot be arylated using copper salts as the promoter, can also be efficiently arylated. In addition, the stereochemistry of these arylation products can be largely retained under the standard conditions.
Hu, Liang,Gui, Qingwen,Chen, Xiang,Tan, Ze,Zhu, Gangguo
supporting information
p. 11070 - 11075
(2016/12/09)

Aluminum oxide mediated C-F bond activation in trifluoromethylated arenes
Thermally activated γ-aluminium oxide was found to be very effective for C-F bond activation in trifluoromethylated arenes. Depending on the activation degree the respective arenes can be converted either to cyclic ketones or to the respective carboxylic acids with good to excellent yields.
Papaianina,Amsharov
p. 1505 - 1508
(2016/01/25)

Bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium]hexabromodipalladate(II); synthesis, characterization, structural study and application as a retrievable heterogeneous catalyst for the amination of aryl halides and Stille cross-coupling reaction
The treatment of tri(p-tolyl)phosphine with 1,2-bis(bromomethyl)benzene results in (2-bromomethylbenzyl)tri(p-tolyl)phosphonium bromide. The resulted phosphonium salt reacts with palladium acetate(II) in a molar ratio of 1.5:1, respectively, to give [(CH3C6H4)3PCH2C6H4CH2OC(O)CH3]2[Pd2Br6], bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium]hexabromodipalladate(II), as a dark brown powder. Characterization of the obtained compound was performed by elemental analysis (CHN), IR, 1H, 31P, 13C NMR and X-ray crystallography techniques. This compound was found to be an efficient catalyst for the amination of aryl halides using aqueous ammonia to produce primary amines and for Stille cross-coupling reaction to produce biphenyl and its derivatives as well. Describe catalyst showed satisfactory results and could be recovered and reused without significant loss of its catalytic activity in both reactions.
Ghorbani-Choghamarani, Arash,Naghipour, Ali,Heidarizadi, Fateme,Shirkhani, Roghayeh,Notash, Behrouz
p. 97 - 102
(2017/12/07)

Synthesis, characterization and structural study of a phosphonium salt containing the [Pd2Br6]2- ion and its application as a novel, efficient and renewable heterogeneous catalyst for amination of aryl halides and the Stille cross-coupling reaction
In this study palladium(II) acetate reacts with a phosphonium salt, [Ph3PCH2C6H4CH2Br]Br, to give [Ph3PCH2C6H4CH2OC(O)CH3]2[Pd2Br6]. Characterization of the obtained compound was performed by elemental analysis, IR, 1H, 31P, 13C NMR and X-ray crystallography. It was found that this compound can act as an efficient catalyst for amination of aryl halides to afford primary amines and satisfactory results were obtained. It has also been successfully employed in the catalytic Stille cross-coupling reaction. The catalyst is easily recoverable and reusable without significant loss of its catalytic activity.
Naghipour, Ali,Ghorbani-Choghamarani, Arash,Heidarizadi, Fateme,Notash, Behrouz
p. 18 - 26
(2016/01/12)