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Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
Ojha, Subhadra,Panda, Niranjan
supporting information
p. 1292 - 1298
(2022/02/19)

Selective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source
The selective α-deuteration of α,β-unsaturated nitriles using the strong base tBuOK or a metal-ligand cooperative Ru pincer catalyst is described. With D2O as deuterium source and glyme as solvent at 70 °C, tBuOK is an efficient catalyst for deuteration at the α-C(sp2) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the tBuOK-catalysed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein's ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst is found to be significantly higher than that of tBuOK, allowing reactions to proceed well even at room temperature. A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using tBuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D2O. (Figure presented.).
Guo, Beibei,de Vries, Johannes G.,Otten, Edwin
supporting information
p. 179 - 186
(2021/10/12)

Cu-catalyzed cyanomethylation of imines and α,β-alkenes with acetonitrile and its derivatives
We describe copper-catalyzed cyanomethylation of imines and α,β-alkenes with a methylnitrile source and provide an efficient route to synthesize arylacrylonitriles and β,γ-unsaturated nitriles. This method tolerates aliphatic and aromatic alkenes substituted with a variety of functional groups such as F, Cl, Br, Me, OMe,tert-Bu, NO2, NH2and CO2H with good to excellent yields (69-98%). These systems consist of inexpensive, simple copper catalyst and acetonitrile with its derivatives (α-bromo/α-iodo-acetonitrile) and are highly applicable in the industrial production of acrylonitriles.
Ahmad, Muhammad Siddique,Ahmad, Atique
p. 5427 - 5431
(2021/02/12)

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
(2021/07/19)

A new palladium heterogeneous complex (Pd-Gu@BOEH): chemoselective, phosphine-free and practical nanocatalyst in carbon–carbon cross-coupling reaction
Herein, boehmite nanoparticles were synthesized via combination of Al(NO3)3·9H2O and NaOH in aqueous solution. This nanomaterial converted to Pd-Gu@BOEH in several sequences. Pd-Gu@BOEH was used as efficient and recoverable nanocatalyst for the chemoselective C–C band formation such as Mizoroki–Heck and Suzuki–Miyaura reactions without any phosphine ligands or inert atmosphere. This catalyst has been characterized by several analyses such as EDS, WDX, SEM, XRD, FT-IR, TEM, TGA, AAS and BET. Also, obtained products from C–C coupling reactions were identified by NMR spectroscopy and their melting points. This catalyst was recycled in described reactions without palladium leaching. The reused catalyst was characterized by EDS, WDX, XRD, FT-IR and AAS analysis, which showed good stability during reaction process.
Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda
p. 1033 - 1049
(2020/11/05)

Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction
A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge
p. 8678 - 8683
(2021/07/26)

Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation
Here we report that chiral Mn(I) complexes are capable of H-P bond activation. This activation mode enables a general method for the hydrophosphination of internal and terminal α,β-unsaturated nitriles. Metal-ligand cooperation, a strategy previously not considered for catalytic H-P bond activation, is at the base of the mechanistic action of the Mn(I)-based catalyst. Our computational studies support a stepwise mechanism for the hydrophosphination and provide insight into the origin of the enantioselectivity.
Pérez, Juana M.,Postolache, Roxana,Casti?eira Reis, Marta,Sinnema, Esther G.,Vargová, Denisa,De Vries, Folkert,Otten, Edwin,Ge, Luo,Harutyunyan, Syuzanna R.
supporting information
p. 20071 - 20076
(2021/12/03)

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists
A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.
Yi, Ce,Xing, Gang,Wang, Siqi,Li, Xiaoran,Liu, Yichuang,Li, Jinyan,Lin, Bin,Woo, Anthony Yiu-Ho,Zhang, Yuyang,Pan, Li,Cheng, Maosheng
(2019/11/26)

Pd–ninhydrin immobilized on magnetic nanoparticles: synthesis, characterization, and application as a highly efficient and recoverable catalyst for Suzuki–Miyaura and Heck–Mizoroki C–C coupling reactions
Abstract: In this work by controlling the interaction between the inorganic complexes and the support material, we have designed a high-activity nanostructured combined of magnetic nanoparticles and Pd–ninhydrin-terminated complex as catalyst. The as-prepared catalyst was characterized by FT-IR, XRD, VSM, SEM, EDAX, ICP, and TGA techniques. This magnetic nanostructure can be used as a novel, green, and efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki C–C coupling reactions. This catalyst showed promising catalytic activity and excellent yields toward various aryliodides and arylbromides in mild reaction conditions. In Suzuki–Miyaura reactions, various aryl halides (I, Br) were coupled with phenyl boronic acids in 5?mg of catalyst and 8?mg of catalyst used for Mizoroki–Heck reaction of aryl halides (I, Br) with n-butyl acrylate or acrylonitrile. The catalyst was reusable and recycled six times without a significant loss in activity and leaching of palladium. Graphic abstract: [Figure not available: see fulltext.].
Hajjami, Maryam,Shirvandi, Zeinab
p. 1059 - 1072
(2020/01/06)

Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones
Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.
Gorbunova, Yelizaveta,Zakusilo, Dmitriy N.,Boyarskaya, Irina A.,Vasilyev, Aleksander V.
(2020/05/25)

Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
Yamamoto, Yuki,Kawaguchi, Shin-Ichi,Nishimura, Misaki,Sato, Yuki,Shimada, Yoshihisa,Tabuchi, Akihiro,Nomoto, Akihiro,Ogawa, Akiya
p. 14684 - 14696
(2020/11/30)

Palladium schiff base complex immobilized on magnetic nanoparticles: An efficient and recyclable catalyst for Mizoroki and Matsuda-Heck coupling
The present work elucidates the catalytic efficiency of palladium Schiff base complex immobilized on amine functionalized magnetic nanoparticles for Heck coupling of structurally different aryl halide/arenediazonium tetrafluoroborate with styrene/acrylate/acrylonitrile. Matsuda-Heck coupling proceeds in aqueous media at room temperature whereas Mizoroki-Heck coupling was carried out at 80 °C. Both reactions were successfully furnished with low catalyst loading. The catalyst was easily separated from reaction mixture and reused up to six times without significant loss of catalytic activity.
Vibhute, Sandip P.,Mhaldar, Pradeep M.,Shejwal, Rajendra V.,Rashinkar, Gajanan S.,Pore, Dattaprasad M.
supporting information

(2020/03/23)

Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions
In this study, the surface of magnetic MCM-41 nanoparticles (MCM-41/Fe3O4) was modified by 3-Aminopropyltriethoxysilane (APTES) and further, 1-methyl imidazole was anchored on their surface using cyanuric chloride as a linker. Then, Pd2+ ions were immobilized on the surface of the modified MCM-41/Fe3O4 (Pd-imi-CC@MCM-41/Fe3O4), and its application was studied as a magnetically recyclable nanocatalyst in carbon-carbon coupling reactions between a wide range of aryl halides and butyl acrylate, methyl acrylate, acrylonitrile, phenylboronic acid, or 3,4-difluorophenylboronic acid under the conditions of a phosphine-free ligand and an air atmosphere. This catalyst has the advantages of both the Fe3O4 nanoparticles and mesoporous MCM-41. The structure of the catalyst was characterized via TEM, SEM, EDS, WDX, N2 adsorption-desorption isotherm, XRD, TGA, FT-IR, and AAS. Also, the recovered catalyst was characterized via SEM, AAS and FT-IR. All the products from the carbon-carbon coupling reaction were obtained with excellent yields and high TON and TOF values, which indicate the high efficiency and activity of this catalyst. The selectivity of this catalyst was studied with various aryl halides bearing different functional groups. Furthermore, the heterogeneity and stability of Pd-imi-CC@MCM-41/Fe3O4 was studied via AAS, and leaching and poisoning tests. According to the results, this heterogeneous catalyst can be reused several times.
Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash
supporting information
p. 14485 - 14501
(2019/09/30)

Ionic Pd/NHC Catalytic System Enables Recoverable Homogeneous Catalysis: Mechanistic Study and Application in the Mizoroki–Heck Reaction
N-Heterocyclic carbene (NHC) ligands are ubiquitously utilized in catalysis. A common catalyst design model assumes strong M–NHC binding in this metal–ligand framework. In contrast to this common assumption, we demonstrate here that lability and controlled cleavage of the M?NHC bond (rather than its stabilization) could be more important for high-performance catalysis at low catalyst concentrations. The present study reveals a dynamic stabilization mechanism with labile metal–NHC binding and [PdX3]?[NHC-R]+ ion pair formation. Access to reactive anionic palladium intermediates formed by dissociation of the NHC ligands and plausible stabilization of the molecular catalyst in solution by interaction with the [NHC-R]+ azolium ion is of particular importance for an efficient and recyclable catalyst. These ionic Pd/NHC complexes allowed for the first time the recycling of the complex in a well-defined form with isolation at each cycle. Computational investigation of the reaction mechanism confirms a facile formation of NHC-free anionic Pd in polar media through either Ph–NHC coupling or reversible H–NHC coupling. The present study formulates novel ideas for M/NHC catalyst design.
Eremin, Dmitry B.,Denisova, Ekaterina A.,Yu. Kostyukovich, Alexander,Martens, Jonathan,Berden, Giel,Oomens, Jos,Khrustalev, Victor N.,Chernyshev, Victor M.,Ananikov, Valentine P.
supporting information

(2019/11/14)

Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
supporting information
p. 7385 - 7389
(2018/06/11)

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
supporting information
p. 2793 - 2796
(2018/06/25)

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
p. 107 - 118
(2017/09/28)

Synthesis of a novel ZnO nanoplates supported hydrazone-based palladacycle as an effective and recyclable heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction
A new hydrazone-based palladacycle complex was successfully prepared onto ZnO nanoplates support and was fully identified by using a variety of methods such as energy dispersive X-ray spectroscopy (EDX), Brunauer-Emmett-Teller analysis (BET), inductively coupled plasma technique (ICP), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR) and X-ray photoelectron spectroscopy (XPS). The morphology of nanoplates support has been also confirmed by scanning electron microscopy (SEM) and powder X-ray diffraction (XRD). Furthermore, it was shown that ZnO nanoplates supported hydrazone-based palladacycle can act as a highly efficient heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction with excellent yields. The reaction was successfully carried out between aryl iodides, bromides or even aryl chlorides with a variety of olefins. Additionally, it is possible to isolate the catalyst from the reaction mixture and reused for eight sequential cycles without remarkable decrease in catalytic activity.
Nouri, Fatemeh,Rostamizadeh, Shahnaz,Azad, Mohammad
p. 664 - 673
(2017/12/15)

Method for synthesizing substituted acrylonitrile with one-pot process
The invention provides a method for synthesizing substituted acrylonitrile with a one-pot process. Beta-aryl substituted acrylonitrile is prepared from 0.01-1.0 mol of aryl substituted methanol or heterocycle substituted methanol as a raw material and a solvent adopting acetonitrile with the concentration of 0.2-2.0 mol/L under the alkaline action. In the oxygen atmosphere, a semiconductor photocatalyst is added, the mixture reacts under assistance of light illumination, and the reaction speed and the yield can be greatly increased. Raw materials for a reaction are easy to obtain, the method is simple and convenient, and the product has important application value.
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Paragraph 0022; 0023; 0024; 0037; 0038; 0039; 0040

(2017/06/02)

Mukaiyama addition of (trimethylsilyl)acetonitrile to dimethyl acetals mediated by trimethylsilyl trifluoromethanesulfonate
(Trimethylsilyl)acetonitrile reacts smoothly with dimethyl acetals in the presence of stoichiometric trimethylsilyl trifluoromethanesulfonate (TMSOTf) to yield β-methoxynitriles. The ideal substrates for this reaction are acetals derived from aromatic aldehydes. Elimination to the corresponding α,β-unsaturated nitriles is observed as the major product in the case of electron-rich acetals. A mechanistic hypothesis that includes isomerization of the silylnitrile to a nucleophilic N-silyl ketene imine is presented.
Downey, C. Wade,Lee, Alice Y.-K.,Goodin, John R.,Botelho, Courtney J.,Stith, William M.
p. 3496 - 3499
(2017/10/05)

A new palladium complex supported on magnetic nanoparticles and applied as an catalyst in amination of aryl halides, Heck and Suzuki reactions
A simple, efficient and less expensive protocol for the phosphine-free C–C coupling reactions and synthesis of anilines in the presence of 2-aminobenzamide complex of palladium supported on Fe3O4 magnetic nanoparticles (Pd(0)-ABA-Fe3O4) has been reported. The Suzuki reaction was carried out in water or PEG using phenylboronic acid (PhB(OH)2) or sodium tetraphenyl borate (NaBPh4). Pd(0)-ABA-Fe3O4 has been found promising for Heck reaction of butyl acrylate, styrene or acrylonitrile with aryl halides (including Cl, Br and I). Also, Pd(0)-ABA-Fe3O4 has been found as efficient catalyst for the amination of aryl halides using aqueous ammonia. The products have been obtained in short reaction times and high yields. The catalyst was easily separated using an external magnet from the reaction mixture and reused for several runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of catalyst has been examined by hot filtration and ICP-OES technique. The nanomagnetical catalyst was characterized by FTIR, TGA, XRD, VSM, TEM, SEM, EDS, DLS and ICP-OES techniques.
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Noori, Nourolah,Ghafouri-nejad, Raziyeh
p. 681 - 693
(2017/01/17)

Synthesis and characterization of a Pd(0) Schiff base complex anchored on magnetic nanoporous MCM-41 as a novel and recyclable catalyst for the Suzuki and Heck reactions under green conditions
A Pd Schiff base complex was immobilized onto the surface of magnetic MCM-41 (Fe3O4@MCM-41@Pd(0)-P2C) as a novel, eco-friendly, and recyclable heterogeneous nanocatalyst and fully characterized by FT-IR, VSM, EDS, transmission electron microscopy, scanning electron microscopy, thermogravimetric analyses, ICP-OES, and X-ray powder diffraction analysis. The Fe3O4@MCM-41@Pd(0)-P2C was investigated as a catalyst for the one-pot Suzuki and Heck reactions in PEG as a green solvent to provide the target products in excellent yields. The main advantages of using this catalyst include a short reaction time, green reaction conditions, a simple experimental procedure, non-use of hazardous organic solvents, low loading of the catalyst, and the ability to use various substrates. More importantly, the catalyst could be easily separated from the reaction mixture with the assistance of an external magnet and could be recovered and reused several times without significant loss of stability and activity.
Nikoorazm, Mohsen,Ghorbani, Farshid,Ghorbani-Choghamarani, Arash,Erfani, Zahra
p. 1413 - 1422
(2017/08/21)

Pd(0)-Arg-boehmite: As Reusable and Efficient Nanocatalyst in Suzuki and Heck Reactions
Abstract: The direct supporting of Pd-arginine complex on boehmite nanoparticles (Pd(0)-Arg-boehmite) was reported as a moisture- and air-stable, heterogeneous, excellent and novel organometallic catalyst, which applied for the Suzuki and Heck cross coupling reactions through coupling of phenylboronic acid, 3,4-difluoro phenylboronic acid, sodium tetraphenyl borate, butyl acrylate, methyl acrylate, acrylonitrile and styrene with a wide range of aryl halide including Cl, Br and I. Pd(0)-Arg-boehmite was prepared for the first time via simple, environmental and inexpensive procedure in water and ethanol without inert atmosphere or high temperature using commercially available materials, and characterized by XRD, TGA, TEM, SEM, EDS and ICP-OES techniques. The leaching of palladium and heterogeneity test of this catalyst was studied by hot filtration and ICP-OES techniques; resulting we found that this catalyst was demonstrated remarkable and excellent recyclability. Graphical Abstract: Boehmite nanoparticles were prepared by inexpensive procedure in water at room temperature and directly immobilized with a new type of Pd-arginine complex. After characterization of this catalyst, its application has been studied for the C–C coupling reactions. [Figure not available: see fulltext.]
Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash
p. 649 - 662
(2017/03/08)

Nickel-Catalyzed C-CN Bond Formation via Decarbonylative Cyanation of Esters, Amides, and Intramolecular Recombination Fragment Coupling of Acyl Cyanides
An efficient nickel-catalyzed decarbonylative cyanation reaction which allows the direct functional-group interconversion of readily available esters into the corresponding nitriles was developed. This reaction successfully offers access to structurally diverse nitriles with high efficiency and excellent functional-group tolerance and provides a good alternative to classical synthetic pathways from diazonium salts or organic halide compounds.
Chatupheeraphat, Adisak,Liao, Hsuan-Hung,Lee, Shao-Chi,Rueping, Magnus
supporting information
p. 4255 - 4258
(2017/08/23)

Preparation method of trans-alpha, beta-unsaturated nitriles compound
The invention relates to a preparation method of a trans-alpha, beta-unsaturated nitriles compound. The method comprises the following steps: uniformly mixing a benzyl alcohol compound, acetonitrile, a promoter and alkali, and carrying out reflux reaction completely to obtain reaction liquid; carrying out conventional extraction, drying, concentration and column chromatographic separation on the reaction liquid in sequence to obtain the trans-alpha, beta-unsaturated nitriles compound. The preparation method belongs to double-component one-boiler reaction, so that conditions are relatively mild, and raw materials are easy to prepare and readily available; the operation is simple, the yield is relatively high, and greenness, environment friendliness and economy can be realized; large-scale production can be realized; the preparation method has an extremely good application potential on the aspect of fine chemicals, and has a relatively good industrial application prospect.
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Paragraph 0018-0020

(2017/05/18)

Synthesis of olefins via a Wittig reaction mediated by triphenylarsine
An arsine-mediated Wittig reaction for the synthesis of olefins is described. After heating triphenylarsine in the presence of an activated alkyl bromide for 30?min, the resulting arsonium salt condensed with aldehydes in as little as 5?min at room temperature, yielding the olefins in high yields. Aromatic, heteroaromatic, and alkyl aldehydes were all suitable substrates for this process.
Li, Lun,Stimac, Jared C.,Geary, Laina M.
supporting information
p. 1379 - 1381
(2017/03/17)

Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)-Catalyzed Synthesis of Primary Pyridinylamines
A relay formalism is proposed herein for categorizing the interplay among reactants, target product, and catalytic center in transition-metal catalysis, an important factor that can dictate overall catalysis viability and efficiency. In this formalism, transition-metal catalysis can proceed by dissociative relay, associative covalent relay, and associative dative relay modes. An intriguing associative covalent relay process operates in rhodium(III)-catalyzed oxadiazolone-directed alkenyl C?H coupling with alkynes and allows efficient access to primary pyridinylamines. Although the primary pyridinylamine synthesis mechanism is posteriori rationalized, the relay formalism formulated herein can provide an important mechanistic conceptual framework for future catalyst design and reaction development.
Yu, Xiaolong,Chen, Kehao,Wang, Qi,Guo, Shan,Zha, Shanke,Zhu, Jin
supporting information
p. 5222 - 5226
(2017/04/27)

Rhodium(III)-catalyzed oxadiazole-directed alkenyl C-H activation for synthetic access to 2-acylamino and 2-amino pyridines
We report herein a Rh(III)-catalyzed alkenyl C-H activation protocol for the coupling of oxadiazoles with alkynes and synthesis of 2- acylamino and 2-amino pyridines, an important heterocyclic scaffold for various naturals products and synthetic pharmaceuticals bearing a readily reacting functional group. The selective protection/deprotection of amino groups through simple solvent switching, good functional group compatibility, superior product yield, and high regioselectivity are some of the notable synthetic features witnessed in this reaction protocol.
Yang, Fan,Yu, Jiaojiao,Liu, Yun,Zhu, Jin
supporting information
p. 9978 - 9987
(2018/05/31)

In-situ-generated palladium nanoparticles in novel ionic liquid: an efficient catalytic system for Heck–Matsuda coupling
Abstract: A green, convenient, ecological and recyclable method comprising dual functionalized, task-specific, ionic liquid (IL)-triggered, in situ-generated Pd nanoparticles (NPs) and their catalytic application for Heck–Matsuda coupling of olefins is described. Both arenediazonium tetrafluoroborate and silica sulphate salts are coupled with olefins under ligand-free and aerobic conditions at ambient temperature furnishing excellent yields of products. The Ionic liquid used acts as a reducing as well as stabilizing agent for in situ-generated Pd NPs. The formed NPs were characterized by transmission electron microscopy (TEM) analysis, having a size below 50?nm, and exhibited high catalytic activity. The catalytic system can be reused for eight times effectively without any significant loss of activity. The method was found to be highly stereo-specific, giving exclusively the ‘E’ isomer.
Gaikwad,Undale,Patil,Pore,Korade,Kamble
p. 4445 - 4458
(2017/07/22)

Palladium-S-propyl-2-aminobenzothioate immobilized on Fe3O4 magnetic nanoparticles as catalyst for Suzuki and Heck reactions in water or poly(ethylene glycol)
A moisture- and air-stable heterogenized palladium catalyst was synthesized by coordination of palladium with S-propyl-2-aminothiobenzamide supported on Fe3O4 magnetic nanoparticles. The prepared nanocatalyst was characterized using Fourier transform infrared, energy-dispersive X-ray and inductively coupled plasma atomic emission spectroscopies, X-ray diffraction, vibrating sample magnetometry, transmission and scanning electron microscopies, dynamic laser scattering and thermogravimetric analysis. This catalyst could be dispersed homogeneously in water or poly(ethylene glycol) and further applied as an excellent nano-organometal catalyst for Suzuki and Heck reactions. The catalyst was easily separated with the assistance of an external magnet from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of catalyst was examined using hot filtration and inductively coupled plasma atomic emission spectroscopy. Also, the effects of various reaction parameters on the Suzuki and Heck reactions are discussed.
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Moradi, Parisa
p. 422 - 430
(2016/05/19)

Immobilized NNN Pd-complex on magnetic nanoparticles: Efficient and reusable catalyst for Heck and Sonogashira coupling reactions
A highly efficient and easily recyclable magnetic nanoparticle supported palladium catalyst was developed and applied in the Heck and Sonogashira reactions in order to show its catalytic applicability in Pd-catalyzed C-C coupling protocols. The catalyst was prepared using a simple chemical process. First, the prepared Fe3O4@SiO2 nanoparticles were reacted with (3-chloropropyl)-trimethoxysilane (3-CPTMS) in order to synthesis chloro-functionalized magnetic nanoparticles (CPS-MNPs). The substitution reaction of synthetic NNN ligand with CPS-MNPs yields the production of CPS-MNPs-NNN ligand. Finally, immobilization of palladium species on CPS-MNPs-NNN ligand surface afforded CPS-MNPs-NNN-Pd catalyst. The structure and morphology of the prepared nanocatalyst was characterized using various methods such as SEM, TEM, XPS, EDX, CHN, ICP, XRD, FT-IR and VSM techniques. The TEM images show that the sizes of the palladium catalyst are in the range of 8-15 nm. The Heck and Sonogashira coupling reactions were performed in the presence of a catalytic amount of this catalyst system (0.5 mol%) and good yields of products were obtained. Due to the magnetic nature of the catalyst it can be separated from the reaction mixture easily by applying an external magnetic field. Heterogeneity tests affirmed that the catalytic activity stayed indefectible during multiple reaction cycles.
Dehghani Firuzabadi, Fahimeh,Asadi, Zahra,Panahi, Farhad
p. 101061 - 101070
(2016/11/09)

Synthesis of a new Pd(0)-complex supported on boehmite nanoparticles and study of its catalytic activity for Suzuki and Heck reactions in H2O or PEG
Boehmite nanoparticles are a cubic orthorhombic structure of aluminum oxide hydroxide containing hydroxyl groups attached to their surface, which were prepared in water using commercially available materials. A moisture- and air-stable palladium S-methylisothiourea complex supported on boehmite nanoparticles (Pd(0)-SMTU-boehmite) was prepared using a very simple and inexpensive procedure without an inert atmosphere using commercially available materials. This nanostructure compound was used as an excellent organometallic catalyst for Suzuki and Heck reactions in H2O or PEG-400. The synthesized nanoparticles were characterized using FT-IR, XRD, BET, TGA, TEM, SEM, EDS and ICP-OES techniques. Nitrogen adsorption/desorption measurements indicated that the boehmite nanoparticles have a BET surface area of about 122.8 m2 g-1. This heterogeneous nanocatalyst was easily separated from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of palladium from the catalyst was examined using hot filtration and ICP-OES techniques.
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Moradi, Parisa
p. 43205 - 43216
(2016/05/24)

Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: Chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles
A copper-catalyzed transfer aldol type reaction of β-hydroxy ketones or nitriles with aldehydes is reported, which enables chemo- and stereoselective access to (E)-α,β-unsaturated ketones and (E)-acrylonitriles. A key step of the in situ copper(i)-promoted retro-aldol reaction of β-hydroxy ketones or nitriles is proposed to generate a reactive Cu(i) enolate or cyanomethyl intermediate, which undergoes ensuing aldol condensation with aldehydes to deliver the products. This reaction uses 1.2 mol% Cu(IPr)Cl (IPr denotes 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) as the catalyst in the presence of 6.0 mol% NaOtBu cocatalyst at room temperature or 70 °C. A range of aryl and heteroaryl aldehydes as well as acrylaldehydes are compatible with many useful functional groups being tolerated. Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine in excellent yields (up to 91%). Finally, a full catalytic cycle for this reaction has been constructed using DFT computational studies in the context of a retro-aldol/aldol two-stage mechanism. A rather flat reaction energy profile is found indicating that both stages are kinetically facile, which is consistent with the mild reaction conditions.
Zhang, Song-Lin,Deng, Zhu-Qin
p. 7282 - 7294
(2016/08/05)

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)

Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles
We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility.
Zhang, Qi,Zhang, Linjing,Tang, Chaojun,Luo, Huan,Cai, Xuediao,Chai, Yonghai
p. 6935 - 6942
(2016/10/14)

Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride to Give α,β-Unsaturated Amides and Alkenyl Nitriles
We have developed a highly selective method for the synthesis of α,β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols have been highly regioselectively transformed to the desired products with good functional group compatibility.
Han, Ya-Ping,Song, Xian-Rong,Qiu, Yi-Feng,Hao, Xin-Hua,Wang, Jia,Wu, Xin-Xing,Liu, Xue-Yuan,Liang, Yong-Min
p. 9200 - 9207
(2015/09/28)

Entangled Cu Complex over Fe3O4@SiO2 as Supported Catalyst for Synthesis of Alkenyl Nitriles with Aromatic Aldehydes and Acetonitrile
An efficient, green and practical approach to synthesize alkenyl nitriles using new supported Cu(II) catalyst via aromatic aldehydes and acetonitrile was developed. The novel catalyst was characterized by FT-IR, XRD, SEM/EDX, TEM, TGA and VSM. Interestingly, the catalyst was found to be active for synthesis of alkenyl nitriles, which were readily obtained in good yields under mild conditions. But most importantly, the original catalyst could be conveniently recovered and recycled from the reaction system by applying an external magnet and reused in four cycles without significant loss in catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
Gu, Zhen,Wang, Yanfang,Yao, Yuan,Xia, Xiaofeng,Wang, Haijun,Li, Wei
p. 2046 - 2054
(2015/12/26)

An Abnormal N-Heterocyclic Carbene-Based Palladium Dimer: Aqueous Oxidative Heck Coupling under Ambient Temperature
Herein we report the synthesis of a new abnormal N-heterocyclic carbene (aNHC)-based ligand and its use in synthesizing an acetate bridged C-H activated palladium dimer (1). In complex 1, the carbene ligand displays an abnormal mode of binding with the palladium(II) ion. We used complex 1 as a catalyst for the oxidative Heck coupling reaction of arylboronic acids with electron-deficient as well as electron-rich olefins at ambient temperature in water to produce selectively the β-arylated products in good to excellent yields.
Hota, Pradip Kumar,Vijaykumar, Gonela,Pariyar, Anand,Sau, Samaresh Chandra,Sen, Tamal K.,Mandal, Swadhin K.
supporting information
p. 3162 - 3170
(2015/11/03)

Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles
An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).
Kumar, Ravi,Arigela, Rajesh K.,Kundu, Bijoy
p. 11807 - 11812
(2015/08/11)

Cu-catalyzed debrominative cyanation of gem-dibromoolefins: A facile access to α,β-unsaturated nitriles
An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, l-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.
Ahuja, Brij Bhushan,Sudalai, Arumugam
p. 5918 - 5923
(2015/06/02)

Highly efficient Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated nitriles
A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).
Yan, Qiaozhi,Kong, Duanyang,Li, Meina,Hou, Guohua,Zi, Guofu
supporting information
p. 10177 - 10181
(2015/09/01)

Palladium(II) supported on polycarbosilane: Application as reusable catalyst for Heck reaction
Heck reaction catalyzed by palladium(II) attached polycarbosilane is reported. Polycarbosilane (PCS), which is an organic-inorganic hybrid polymer containing both Si and C in its back bone structure, was synthesized by the polycondensation of trichloromethylsilane and trimethoxyvinylsilane in the presence of sodium metal. Palladium acetate was attached to the polycarbosilane (Pd-PCS) and its catalytic activity was investigated. Heck reaction in which C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base has been selected for the study. Palladium ions supported on PCS have been used as a catalyst for the first time and it efficiently catalyzed Heck reaction and an yield of 75-90% was obtained with different substrates. For comparison, catalytic activities of Pd ions supported on SBA-15, activated charcoal and amorphous silica were also investigated. Results indicate the superior activity of Pd-PCS.
Mangala, Kunniyur,Sinija,Sreekumar, Krishnapillai
p. 87 - 92
(2015/07/07)

Bronsted acid mediated nitrogenation of propargylic alcohols: An efficient approach to alkenyl nitriles
A novel and efficient approach to alkenyl nitriles from readily available propargylic alcohols has been developed. This nitrogenation reaction is transition-metal-free and could be conducted under air at ambient temperature, which makes this protocol promising and practical. Moreover, NH4Br is disclosed as an efficient additive to promote the stereoselectivity of this reaction. the Partner Organisations 2014.
Huang, Xiaoqiang,Jiao, Ning
supporting information
p. 4324 - 4328
(2014/06/23)

Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base
The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.
Huang, Wenhua,Zhao, Shuang-Hong,Dong, Guang-Ping
supporting information
p. 1802 - 1810
(2015/10/29)

Phosphine-free tetradentate salicylaldimine ligand complexed with palladium: First application in heck reactions
Heck reactions were carried out using phosphine-free tetradentate salicylaldimine ligand complexed with PdCl2 under mild reaction conditions, short reaction time, and low palladium loading. All aryl iodides underwent coupling reactions with olefins, giving corresponding trans-products, with good to excellent yields, whereas aryl bromides gave very poor yields and aryl chlorides failed to react.
Kalhapure, Rahul S.,Govender, Thirumala,Akamanchi, Krishnacharya G.
p. 3337 - 3345
(2015/10/06)

Highly Z-selective synthesis of a,b-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction
A new HWE reagent, (o-tBuC6H4O)2P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-a,bunsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z-olefins with extremely high selectivity. The combination of t-BuOK and 18-crown-6 (1 equiv) is the base of choice for aromatic aldehydes and t-BuOK is generally the base of choice for aliphatic aldehydes.
Ando, Kaori,Okumura, Miho,Nagaya, Shigeo
p. 2026 - 2028
(2013/04/23)

Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles
Various aryl bromides were efficiently converted into the corresponding aromatic nitriles in good yields by the treatment with Mg turnings and subsequently DMF, followed by treatment with molecular iodine and aq NH 3. The same treatment of aryl bromides, which are weakly reactive to Mg turnings, with iPrMgCl·LiCl and subsequently DMF, followed by the treatment with molecular iodine and aq NH3 also afforded the corresponding aromatic nitriles in good yields. On the other hand, when N-formylpiperidine was used instead of DMF, p-substituted β-bromostyrenes were converted into the corresponding p-substituted cinnamonitriles, i.e., α,β-unsaturated nitriles, in good to moderate yields by the same procedure. The reactions were carried out by means of a simple experimental procedure and did not require any toxic metal cyanides or expensive rare metals. Therefore, the present reactions are practical and environmentally benign one-pot methods for the preparation of aromatic nitriles, cinnamonitriles, and aliphatic nitriles from aryl bromides, β-bromostyrenes, and alkyl bromides, respectively, through the formation of Grignard reagents and their DMF or N-formylpiperidine adducts.
Ishii, Genki,Harigae, Ryo,Moriyama, Katsuhiko,Togo, Hideo
p. 1462 - 1469
(2013/02/25)

Synthesis of homotaurine and 1-substituted homotaurines from α,β-unsaturated nitriles
Homotaurine and a series of 1-substituted homotaurines were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to aliphatic and aromatic α,β-unsaturated nitriles followed by lithium aluminum hydride mediated reduction and performic acid oxidation. The synthesis of 1,1-disubstituted homotaurines was attempted with β,β-disubstituted acrylonitriles as starting materials but failed due to steric hindrance. The current process is an efficient method for the synthesis of 1-substituted homotaurines. Georg Thieme Verlag Stuttgart New York.
Ma, Yunhai,Xu, Jiaxi
experimental part
p. 2225 - 2230
(2012/09/22)

A novel oxidative transformation of alcohols to nitriles: An efficient utility of azides as a nitrogen source
An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H 2O.
Rokade, Balaji V.,Malekar, Sanjeev K.,Prabhu, Kandikere Ramaiah
p. 5506 - 5508
(2012/07/03)

Metal-polymer hybrid material as a catalyst for the heck coupling reaction under phosphine-free conditions
A method is described for making a poly-aminophenol-based hybrid material by in situ polymerization of aminophenol using palladium acetate as the oxidant. The oxidative polymerization of aminophenol leads to the formation of poly-aminophenol, while the reduction of palladium acetate results in the formation of palladium nanoparticles. The palladium nanoparticles were found to be highly dispersed and stabilized throughout the polymer matrix. The hybrid nanocomposite material showed excellent catalytic efficiency with respect to a Heck coupling reaction at a relatively low temperature and under flexible conditions.
Ul Islam, Rafique,Witcomb, Michael J.,Scurrell, Michael S.,Van Otterlo, Willem,Van Der Lingen, Elma,Mallick, Kaushik
experimental part
p. 3561 - 3572
(2011/10/02)