- Syntheses and Optical Properties of Azo-Functionalized Ruthenium Alkynyl Complexes
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The syntheses of trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-C≡C-1-C6H4-4-NO2)Cl(L2)2] (L2=dppm (Ru1), dppe) (Ru2)), trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-(E)-CH=CH-1-C6H4-4-NO2)Cl(dppe)2] (Ru3), and trans-[Ru(C≡C-1-C6H4-4-(E)-CH=CH-1-C6H2-2,6-Et2-4-N=N-1-C6H4-4-NO2)Cl(dppe)2] (Ru4) are reported, together with those of precursor alkynes. Their electrochemical properties were assessed by cyclic voltammetry (CV), linear optical and quadratic nonlinear optical (NLO) properties assayed by UV/Vis-NIR spectroscopy and hyper-Rayleigh scattering studies at 1064 nm, respectively, and their linear optical properties in the formally RuIII state examined by UV/Vis-NIR spectroelectrochemistry. These data were compared to those of analogues with E-ene and yne linkages in place of the azo groups. Computational studies using time-dependent density functional theory were undertaken on model compounds (Ru2′–Ru4′) to rationalize the optical behaviour of the experimental complexes.
- Wei, Dilan,Kodikara, Mahesh S.,Morshedi, Mahbod,Moxey, Graeme J.,Wang, Huan,Wang, Genmiao,Quintana, Cristóbal,Zhang, Chi,Stranger, Rob,Cifuentes, Marie P.,Humphrey, Mark G.
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Read Online
- Preparation of nitriles from aldehydes using ammonium persulfate by means of a nitroxide-catalysed oxidative functionalisation reaction
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A methodology for the preparation of nitriles from aldehydes by means of an oxidative functionalisation reaction is reported. It employs ammonium persulfate as both the primary oxidant and the nitrogen source, and a catalytic amount of a nitroxide. It is applicable to a range of structurally diverse (hetero)aromatic aldehydes furnishing the nitrile products in 30-97% isolated yield. Given the ready accessibility of aldehydes and that ammonium persulfate is cheap and less toxic than many other reagents for generating nitriles, this methodology offers a simple and easy to use approach to this valuable class of compounds. This journal is
- León Sandoval, Arturo,Politano, Fabrizio,Witko, Mason L.,Leadbeater, Nicholas E.
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supporting information
p. 667 - 671
(2022/01/28)
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- Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
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Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
- Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
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p. 4460 - 4467
(2022/03/15)
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- Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation
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Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.
- Wang, Shengyu,Wang, Jianqiang,Pan, Junyi,Liu, Cheng,Gong, Xubin,Guo, Cheng
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- Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
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A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
- Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
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p. 9561 - 9568
(2021/08/06)
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- Pd/CoFe2O4/chitosan: A highly effective and easily recoverable hybrid nanocatalyst for synthesis of benzonitriles and reduction of 2-nitroaniline
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In this study, a novel catalyst system with high activity and easy recoverability was successfully prepared through the deposition of Pd nanoparticles (NPs) onto designed sustainable hybrid beads containing magnetic cobalt ferrite and chitosan (Pd/CoFe2O4/chitosan). The catalytic potential of Pd/CoFe2O4/chitosan hybrid nanocatalyst was then assessed in i) preparation of benzonitriles via aryl halides cyanation and ii) reduction of 2-nitroaniline (2-NA). Various aryl iodides and bromides were successfully cyanated by Pd/CoFe2O4/chitosan hybrid nanocatalyst with excellent reaction yields within 3 h. In addition to the production of benzonitriles, the hybrid nanocatalyst showed excellent activity by reducing 2-NA in 65 s. It was proved that the Pd/CoFe2O4/chitosan hybrid nanocatalyst outperformed many catalysts used in the cyanation of aryl halides and catalytic reduction of 2-NA previously reported in the literature. Moreover, it was found that the designed Pd/CoFe2O4/chitosan hybrid nanocatalyst was easily and effectively separated from the reaction mixture using an external magnet and reused several times in catalytic reactions without considerable loss of catalytic activity.
- Baran, Talat,Nasrollahzadeh, Mahmoud
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- An easily fabricated palladium nanocatalyst on magnetic biochar for Suzuki-Miyaura and aryl halide cyanation reactions
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Biochar is a carbon-rich solid, the surface of which is covered with a high density of functional carbonyl, hydroxyl and carboxylic acid groups. In this work, palladium nanoparticles were embedded on magnetic biochar and a new reusable and environmentally-friendly catalyst was developed and applied for the promotion of Suzuki-Miyaura C-C coupling and cyanation reactions. The high-carbon (77%), low-ash content (5.8%) and the relatively high surface area (266 m2g?1) of pine tree biochar (PTB) suggested that it might be highly suitable as a catalyst substrate. The Fe3O4-Pd-biochar nanocomposite was successfully characterized using SEM, TEM, EDX, FT-IR, BET and XRD. Its catalytic role was initially evaluated usingp-NO2C6H4I as a model reactant (for both types of reactions) and later for the production of biaryls and benzonitriles from a wide range of aryl halides under mild reaction conditions. Biaryls and benzonitriles were characterized using GC-MS. In the case of the Suzuki-Miyaura reaction, the optimum yield of 98% was obtained with a catalyst concentration of 0.04 mol%, microwave irradiation of 400 W, and a residence time of 5 min, using K2CO3as the base. With respect to the cyanation reaction, dimethylformamide, Na2CO3and 6 h were the optimum solvent, base and reaction duration, respectively. Subsequently, the nanocatalyst showed excellent catalytic activity in both reactions, achieving >88% yields in most cases, regardless of the aryl iodide or bromide used and the type of substitution.
- Akay, Sema,Baran, Talat,Kalderis, Dimitrios,Kayan, Berkant,Tsubota, Toshiki,Turun?, Ersan
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p. 12519 - 12527
(2021/07/25)
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- Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide
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Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]
- Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng
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- Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media
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Abstract: Pd–N-heterocyclic carbine complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA, and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K4[Fe(CN)6]·3H2O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst confers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, ease of the catalyst recovery and reuse by magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles. Graphic Abstract: A new water dispersible heterogeneous Pd–N-heterocyclic carbene for the efficient fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water is developed.[Figure not available: see fulltext.].
- Chahkamali, Farhad Omarzehi,Sansano, José Miguel,Sobhani, Sara
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- Zinc Oxide/Graphene Oxide as a Robust Active Catalyst for Direct Oxidative Synthesis of Nitriles from Alcohols in Water
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In this work, without using any linker or chemical modification of graphene oxide, a zinc oxide immobilized graphene oxide-based catalyst was used for the direct aerobic oxidative conversion of alcohols to the nitriles in water. In the first step, graphene oxide was prepared and then zinc ions were electrostatically adsorbed onto the surface of graphene oxide. In the following step, zinc oxide nanoparticles were generated via in-situ growth in presence of NaOH. It was illustrated that graphene oxide layers can control the size of in-situ generated zinc oxide nanoparticles. Various aromatic/aliphatic/heteroaromatic primary alcohols converted to the nitriles in high yields under O2 balloon with ZnO/GO catalyst. This catalyst can be used for 7 successful consecutive runs without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]
- Sarvi, Iraj,Zahedi, Ehsan
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- Selective oxidation of alcohols to nitriles with high-efficient Co-[Bmim]Br/C catalyst system
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An efficient method for catalyzing the ammoxidation of aromatic alcohols to aromatic nitriles was developed, in which a new heterogeneous catalyst based on transition metal elements was employed, the new catalyst was named Co-[Bmim]Br/C-700 and then characterized by X-ray photo-electronic spectroscopy, transmission electron microscope and X-ray diffraction. The reaction was carried out by two consecutive dehydrogenations under the catalysis of Co-[Bmim]Br/C-700, which catalytically oxidized the alcohol to the aldehyde, and then the aldehyde was subjected to ammoxidation to the nitrile. The catalyst system was suitable for a wide range of substrates and nitriles obtained in high yields, especially, the conversion rate of benzyl alcohol, 4-methoxybenzyl alcohol, 4-chlorobenzyl alcohol and 4-nitrobenzyl alcohol reached 100%. The substitution of ammonia and oxygen for toxic cyanide to participate in the reaction accords with the theory of green chemistry.
- Xia, Yu-Yan,Lv, Qing-Yang,Yuan, Hua,Wang, Jia-Yi
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p. 3957 - 3964
(2021/04/09)
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- A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide
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This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.
- ULUDAG, Nesimi,GIDEN, Ozge NUR
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p. 993 - 998
(2021/02/05)
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- Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst
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Trichloroacetonitrile has been found to be an efficient dehydrating agent for a range of aldoximes including aromatic and heterocyclic aldoxime yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction.
- Ma, Xiaoyun,Liu, Dan,Chen, Zhengjian
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p. 3261 - 3266
(2021/06/30)
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- Nitration of deactivated aromatic compounds via mechanochemical reaction
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A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.
- Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
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supporting information
(2021/05/05)
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- Efficient nitriding reagent and application thereof
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The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0212-0214
(2021/03/31)
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- Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**
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The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.
- Murugesan, Kathiravan,Donabauer, Karsten,K?nig, Burkhard
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supporting information
p. 2439 - 2445
(2020/12/07)
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- Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets
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Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.
- Hua, Manli,Song, Jinliang,Huang, Xin,Liu, Huizhen,Fan, Honglei,Wang, Weitao,He, Zhenhong,Liu, Zhaotie,Han, Buxing
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supporting information
p. 21479 - 21485
(2021/08/23)
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- Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
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A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
- Pal, Shantanu,Sahoo, Subrata
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p. 18067 - 18080
(2021/12/06)
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- A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes
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The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.
- Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe
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p. 7176 - 7185
(2021/06/30)
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- Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate
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The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration.
- Gr?ger, Harald,Nonnhoff, Jannis
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- Revisiting the synthesis of aryl nitriles: a pivotal role of CAN
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Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN?leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.
- Saikia, Rakhee,Park, Kwihwan,Masuda, Hayato,Itoh, Miki,Yamada, Tsuyoshi,Sajiki, Hironao,Mahanta, Sanjeev P.,Thakur, Ashim J.
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p. 1344 - 1351
(2021/02/27)
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- Unprecedented Catalysis of Cs+Single Sites Confined in y Zeolite Pores for Selective Csp3-H Bond Ammoxidation: Transformation of Inactive Cs+Ions with a Noble Gas Electronic Structure to Active Cs+Single Sites
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We report the transformation of Cs+ ions with an inactive noble gas electronic structure to active Cs+ single sites chemically confined in Y zeolite pores (Cs+/Y), which provides an unprecedented catalysis for oxidative cyanation (ammoxidation) of Csp3-H bonds with O2 and NH3, although in general, alkali and alkaline earth metal ions without a moderate redox property cannot activate Csp3-H bonds. The Cs+/Y catalyst was proved to be highly efficient in the synthesis of aromatic nitriles with yields >90% in the selective ammoxidation of toluene and its derivatives as test reactions. The mechanisms for the genesis of active Cs+ single sites and the ammoxidation pathway of Csp3-H bonds were rationalized by density functional theory (DFT) simulations. The chemical confinement of large-sized Cs+ ions with the pore architecture of a Y zeolite supercage rendered the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap reduction, HOMO component change, and preferable coordination arrangement for the selective reaction promotion, which provides a trimolecular assembly platform to enable the coordination-promoted concerted ammoxidation pathway working closely on each Cs+ single site. The new reaction pathway without involvement of O2-dissociated O atom and lattice oxygen differs from the traditional redox catalysis mechanisms for the selective ammoxidation.
- Acharyya, Shankha S.,Ghosh, Shilpi,Iwasawa, Yasuhiro,Kaneko, Takuma,Sasaki, Takehiko,Yoshida, Yusuke
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p. 6698 - 6708
(2021/06/25)
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- Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid
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The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.
- Baucom, Kyle D.,Brown, Derek B.,Caille, Seb,Murray, James I.,Quasdorf, Kyle,Silva Elipe, Maria V.
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supporting information
(2021/06/30)
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- Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile
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A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.
- Liu, Si-Zhan,Li, Jing,Xue, Cao-Gen,Xu, Xue-Tao,Lei, Lin-Sheng,Huo, Chen-Yu,Wang, Zhen,Wang, Shao-Hua
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supporting information
(2021/02/01)
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- Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis
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A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.
- De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio
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- Ruthenium(II)-Complex-Catalyzed Acceptorless Double Dehydrogenation of Primary Amines to Nitriles
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Acceptorless dehydrogenative oxidation of primary amines into nitriles using an in situ complex derived from commercially available dichloro(1,5-cyclooctadiene) ruthenium(II) complex and simple hexamethylenetetramine has been demonstrated. The synthetic protocol is highly selective and yields the nitrile compounds in moderate to excellent yields and produces hydrogen as the sole byproduct.
- Kannan, Muthukumar,Muthaiah, Senthilkumar
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supporting information
p. 1073 - 1076
(2020/07/04)
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- Acceptorless dehydrogenation of amines and alcohols using simple ruthenium chloride
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A highly efficient, economic and environmental friendly catalyst system has been developed for the dehydrogenation of alcohols and amines using simple RuCl3·nH2O and N-benzylhexamethylenetetramine. The in situ catalyst system efficiently oxidized the primary and secondary amines and secondary alcohols into nitrile, imine and ketone products, respectively in moderate to excellent yields. The developed catalyst system was also found to be efficient for the dehydrogenation of N-heterocyles. A detailed mechanism study revealed the first example of N-benzylhexamethylenetetramine (HMTA-Bz) being simultaneously acting as base, reducing agent and hydride source to generate the [Ru(II)(H)2] species as the active catalyst. The mechanism studies also revealed both the alcohol and amine oxidation involves dehydrogenative pathway with the evolution of hydrogen as the only by-product. The developed catalyst system also provides possible platform for the release of hydrogen from liquid organic hydrogen carriers (LOHCs).
- Barteja, Parul,Devi, Preeti,Kannan, Muthukumar,Muthaiah, Senthilkumar
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- Method for continuous preparation of nitriles in a pipelined reactor (by machine translation)
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The method comprises the following steps that a tin catalyst is coated on the inner wall of the pipeline reactor; and the method comprises the following steps: coating a tin catalyst on the inner wall of the pipeline reactor. The amide solution and the catalytic auxiliary agent are mixed and then sent to a pipeline reactor, and the amide is dehydrated to generate nitrile at the reaction pressure of 0.1 - 2.0 mpa and 100 - 200 °C reaction temperature. The resulting reaction product was separated to give the crude product of the nitrile to which the amide corresponded. In the pipeline reactor, the corresponding nitrile is continuously prepared under the action of the tin catalyst, a dehydrating agent is not needed, byproducts only are water, and three wastes are reduced. (by machine translation)
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Paragraph 0036-0047; 0056-0057
(2020/12/14)
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- Pd NPs?Fe3O4/chitosan/pumice hybrid beads: A highly active, magnetically retrievable, and reusable nanocatalyst for cyanation of aryl halides
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In this study, Fe3O4/chitosan/pumice hybrid beads were developed as a new stabilizer agent, and palladium nanoparticles (Pd NPs) were successfully decorated on the designed stabilizer without adding any toxic reducing resource. Then, the potential use of Pd NPs?Fe3O4/chitosan/pumice hybrid beads as a heterogeneous catalyst against different aryl halide cyanations was investigated with K4[Fe(CN)6]. In these reactions, Pd NPs? Fe3O4/chitosan /pumice hybrid beads showed high catalytic activity by converting aryl halides to the desired benzonitriles with high product yields (80 %–98 %). Due to the magnetically separable nature of Pd NPs?Fe3O4/chitosan/pumice hybrid beads, they were reused several times, and 86 % yield was obtained even after six successive runs. This paper reveals that Pd NPs?Fe3O4/chitosan/pumice hybrid beads have a high potential to synthesis a broad range of nitriles due to their excellent catalytic and retrievable capability.
- Baran, Talat
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- Earth-Abundant Bimetallic Nanoparticle Catalysts for Aerobic Ammoxidation of Alcohols to Nitriles
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Heterogeneous nitrogen-doped carbon-incarcerated iron/copper bimetallic nanoparticle (NP) catalysts prepared from nitrogen-containing polymers were developed. These catalysts showed activity higher than that of the corresponding monometallic NPs for aerobic ammoxidation of alcohols to nitriles. The important procedure for high activity in the catalyst preparation was found to be a simultaneous reduction of two metal salts.
- Kobayashi, Shu,Yang, Xi,Yasukawa, Tomohiro
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p. 7543 - 7548
(2020/06/27)
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- Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical
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This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.
- Shee, Maniklal,Shah, Sk. Sheriff,Singh, N. D. Pradeep
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supporting information
p. 14070 - 14074
(2020/10/12)
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- Iron-Promoted Decarboxylation of Arylacetic Acids for the Synthesis of Aromatic Nitriles with Sodium Nitrite as the Nitrogen Source
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A new and effective method was developed for the synthesis of aromatic nitriles from arylacetic acids by using NaNO 2as the nitrogen source and Fe(OTf) 3as the promoter at 50 °C. A series of arylacetic acids underwent this transformation to give the targeted products in yields of 51-90%. Because of the mild conditions, the reaction is compatible with a broad range of functional groups, including ester, carboxy, hydroxy, acetamido, halo, nitro, cyano, methoxy, and even highly reactive formyl groups.
- Shen, Zhenpeng,Liu, Wenbo,Tian, Xinzhe,Zhao, Zhe,Ren, Yun-Lai
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supporting information
p. 1805 - 1808
(2020/11/02)
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- Acetic Anhydride-Acetic Acid as a New Dehydrating Agent of Aldoximes for the Preparation of Nitriles: Preparation of 2-Cyanoglycals
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Glycals, 1,2-unsatrated carbohydrates, are versatile building blocks for the synthesis of various scaffolds. Despite their potential to serve as suitable precursors in diversity-oriented synthesis, 2-cyanoglycals are less explored in terms of their synthesis and derivatization. Herein, we report a combination of Ac 2 O and AcOH as new and efficient dehydrating agent of aldoximes for the synthesis of 2-cyanoglycals. In comparison to the conventional dehydrating system of Ac 2 O-base (such as NaOH, NaOAc and K 2 CO 3), the current protocol provides superior yields and faster reaction rates. The scope and limitations of the dehydrating system are investigated.
- Kinfe, Henok H.,Mabasa, Jackie,Mabasa, Tommy F.,Makhubela, Banothile C. E.,Simelane, Mthokozisi,Vatsha, Banele
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supporting information
p. 991 - 996
(2020/06/10)
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- HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles
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We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is
- Hammond, Gerald B.,Mudshinge, Sagar R.,Potnis, Chinmay S.,Xu, Bo
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supporting information
p. 4161 - 4164
(2020/07/14)
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- Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides
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A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.
- Murata, Yuki,Iwasa, Hitomi,Matsumura, Mio,Yasuike, Shuji
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p. 679 - 681
(2020/07/30)
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- Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles
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Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.
- Xu, Jiaxi,Gao, Yu,Li, Zhenjiang,Liu, Jingjing,Guo, Tianfo,Zhang, Lei,Wang, Haixin,Zhang, Zhihao,Guo, Kai
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p. 311 - 315
(2020/01/25)
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- An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions
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Abstract: A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.
- Uludag, N.
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p. 1640 - 1645
(2020/10/22)
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- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
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A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
- Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
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p. 17288 - 17292
(2020/05/18)
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- An Air-Stable N-Heterocyclic [PSiP] Pincer Iron Hydride and an Analogous Nitrogen Iron Hydride: Synthesis and Catalytic Dehydration of Primary Amides to Nitriles
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An air-stable N-heterocyclic PSiP pincer iron hydride FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) (4) was synthesized by Si-H activation of a Ph-substituted [PSiP] pincer ligand. The analogous strong electron-donating iPr-substituted [PSiP] pincer ligand was prepared and introduced into iron complex to give an iron nitrogen complex FeH(N2)(PMe3)(SiPh(NCH2PiPr2)2C6H4) (6). Both 4 and 6 showed similar high efficiency for catalytic dehydration of primary amides to nitriles. Air-stable iron hydride 4 was the best catalyst for its stabilization and convenient preparation. A diverse range of cyano compounds including aromatic and aliphatic species was obtained in moderate to excellent yields. A plausible catalytic reaction mechanism was proposed.
- Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Wang, Yajie,Xie, Shangqing,Zhang, Hua
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- Method for continuous preparation of nitriles by amides (by machine translation)
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The method comprises the following steps: preparing a lead salt supported by a molecular sieve by a lead salt and a molecular sieve through an impregnation method; and filling a molecular sieve-loaded lead catalyst into a fixed bed reactor. The amide or amide solution is sent into a fixed bed reactor from the top of the fixed bed to be subjected to catalytic dehydration, and the obtained reaction product is led out from the bottom of the fixed bed. The reaction product is separated to obtain the crude product of the nitrile corresponding to the amide. A fixed bed continuous production process is adopted, the reaction process is simple, the production efficiency is high, the product post-treatment is simple, and industrial production is easy to realize. (by machine translation)
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Paragraph 0033-0054; 0061-0065
(2020/12/15)
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- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
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The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
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supporting information
p. 281 - 285
(2020/01/28)
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- On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine
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Herein, we demonstrate the on-demand synthesis of chloramine from aqueous ammonia and sodium hypochlorite solutions, and its subsequent utilization as an ambiphilic nitrogen source in continuous-flow synthesis. Despite its advantages in cost and atom economy, chloramine has not seen widespread use in batch synthesis due to its unstable and hazardous nature. Continuous-flow chemistry, however, provides an excellent platform for generating and handling chloramine in a safe, reliable, and inexpensive manner. Unsaturated aldehydes are converted to valuable aziridines and nitriles, and thioethers are converted to sulfoxides, in moderate to good yields and exceedingly short reaction times. In this telescoped process, chloramine is generated in situ and immediately used, providing safe and efficient conditions for reaction scale-up while mitigating the issue of its decomposition over time.
- Danahy, Kelley E.,Styduhar, Evan D.,Fodness, Aria M.,Heckman, Laurel M.,Jamison, Timothy F.
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supporting information
p. 8392 - 8395
(2020/11/18)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 3583 - 3588
(2020/08/05)
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- Bis(phenoxy-imine) ruthenium(II) carbonyl complexes: syntheses, structures and their catalytic activities for conversion of aldehydes to nitriles
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Three new ruthenium(II) carbonyl complexes that bear phenoxy-imine chelate ligands, [RN = CH(C6H4O)]2Ru(CO)2 (1: R = 2,6-Me2C6H3; 2: R = 4-OMeC6H4; 3: R = 4-ClC6H4) have been synthesized. These mononuclear ruthenium(II) complexes were fully characterized by elemental analysis, FT?IR, and 1H and 13C NMR. Furthermore, the molecular structures of 1-3 were determined by X-ray crystal diffraction analysis. In the presence of NaHCO3 as the base, the Ru carbonyl complexes showed moderate to good catalytic activities for the conversion of aldehydes to nitriles via the dehydration of aldoximes.
- Hao, Zhi-Qiang,Li, Ying,Ma, Dong-Zhu
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- Difluorocarbene-Based Cyanation of Aryl Iodides
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A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.
- Cao, Yu-Cai,Du, Ruo-Bing,Fu, Zhi-Hong,Guo, Yu,Lin, Jin-Hong,Xiao, Ji-Chang,Xiao, Xuan,Yao, Xu,Zhang, Yin-Xiang,Zheng, Xing
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supporting information
p. 713 - 717
(2020/04/08)
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- An aerobic and green C-H cyanation of terminal alkynes
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This study describes a benign C-H cyanation of terminal alkynes with α-cyanoesters serving as a nontoxic cyanide source. In situ generation of the key copper cyanide intermediate is proposed by a sequence of α-C-H oxidation and copper-mediated β-carbon elimination of α-cyanoesters, releasing the α-ketoester byproduct observed experimentally. The ensuing reaction of copper cyanide with terminal alkynes delivers preferentially cyanoalkynes and surpasses the possible Glaser type dimerization of terminal alkynes or the undesired accumulation of HCN under protic conditions. The presence of the co-oxidant K2S2O8 is crucial to this selectivity, probably by promoting oxidative transmetalation and the resulting formation of the Cu(iii)(acetylide)(CN) intermediate. All the reagents and salts used are commercially available, cheap and nontoxic, avoiding the use of highly toxic cyanide salts typically required in cyanation studies. The scope of this reaction is demonstrated with a set of alkynes and α-cyanoesters. The application of this method to late-stage functionalization of the terminal alkyne group in an estrone derivative is also feasible, showing its practical value for drug design.
- Si, Yi-Xin,Zhang, Song-Lin,Zhu, Peng-Fei
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supporting information
p. 9216 - 9220
(2020/12/03)
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- Palladium-Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source
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A new source of “CN” employing formamide and cyanuric chloride is introduced for the cyanation reactions. The treatment of formamide and 2,4,6-trichloro-1,3,5-triazine (TCT; cyanuric chloride) afforded an efficient cyanating agent which it can be used as a nontoxic, readily available, and non-expensive reagent in the cyanation transformations. In this study, palladium-catalyzed cyanation of aryl halides was successfully accomplished using this new “CN” source in high yields.
- Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
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p. 2699 - 2707
(2020/04/08)
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- Efficient dehydration of primary amides to nitriles catalyzed by phosphorus-chalcogen chelated iron hydrides
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A series of phosphorus-chalcogen chelated hydrido iron (II) complexes 1–7, (o-(R'2P)-p-R-C6H4Y)FeH (PMe3)3 (1: R = H, R' = Ph, Y = O; 2: R = Me, R' = Ph, Y = O; 3: R = H, R' = iPr, Y = O; 4: R = Me, R' = iPr, Y = O; 5: R = H, R' = Ph, Y = S; 6: R = Me, R' = Ph, Y = S; 7: R = H, R' = Ph, Y = Se), were synthesized. The catalytic performances of 1–7 for dehydration of amides to nitriles were explored by comparing three factors: (1) different chalcogen coordination atoms Y; (2) R' group of the phosphine moiety; (3) R substituent group at the phenyl ring. It is confirmed that 5 with S as coordination atom has the best catalytic activity and 7 with Se as coordination atom has the poorest catalytic activity among complexes 1, 5 and 7. Electron-rich complex 4 is the best catalyst among the seven complexes and the dehydration reaction was completed by using 2 mol% catalyst loading at 60 °C with 24 hr in the presence of (EtO)3SiH in THF. Catalyst 4 has good tolerance to many functional groups. Among the seven iron complexes, new complexes 3 and 4 were obtained via the O-H bond activation of the preligands o-iPr2P(C6H4)OH and o-iPr2P-p-Me-(C6H4)OH by Fe(PMe3)4. Both 3 and 4 were characterized by spectroscopic methods and X-ray diffraction analysis. The catalytic mechanism was experimentally studied and also proposed.
- Li, Kai,Sun, Hongjian,Yang, Wenjing,Wang, Yajie,Xie, Shangqing,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
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- Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction
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The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.
- Shah, Sk. Sheriff,Shee, Maniklal,Singh, N. D. Pradeep
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supporting information
p. 4240 - 4243
(2020/04/22)
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- Green synthesis of palladium nanocatalyst derived from the β-cyclodextrin used as effective heterogeneous catalyst for cyanation of aryl halides
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In this study, preparation of highly stable palladium nanoparticles (Pd NPs) on Schiff base modified β-cyclodextrin (β-CD-Sch) in the absence of reducing agents has been successfully carried out. Pd NPs&at;β-CD-Sch has then been applied as nanocatalyst in the synthesis of benzonitriles via cyanation reaction using K4Fe(CN)6, which is a low cost, commercially available and non-toxic cyanide source. A series of benzonitriles containing different substrates were successfully fabricated with 77–98percent yields using Pd NPs&at;β-CD-Sch. Moreover, Pd NPs&at;β-CD-Sch catalyst was quantitatively recovered and reutilized several times, showing good reaction yields. This work revealed that i) prepared β-CD-Sch is an effective stabilizer for the fabrication of Pd NPs and ii) Pd NPs&at;β-CD-Sch catalyst play an important role in the fabrication of benzonitriles.
- Baran, Talat,Nasrollahzadeh, Mahmoud
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