- Highly active, low-valence molybdenum- and tungsten-amide catalysts for bifunctional imine-hydrogenation reactions
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The reactions of [M(NO)(CO)4(ClAlCl3)] (M=Mo, W) with (iPr2PCH2CH2)2NH, (PNHP) at 90 °C afforded [M(NO)(CO)(PNHP)Cl] complexes (M=Mo, 1 a; W, 1 b). The treatment of co
- Chakraborty, Subrata,Blacque, Olivier,Fox, Thomas,Berke, Heinz
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- Ullmann-type C-N coupling reaction catalyzed by CuI/metformin
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A facile and efficient method for Ullmann-type C-N coupling reaction of amine and aryl halide catalyzed by CuI/metformin in EtOH is described. The advantages of this method are the use of an inexpensive and readily available catalyst and ligand, easy workup, shorter reaction time, improved yields, and the use of green solvent. Furthermore, this procedure is applied successfully for the modification of natural products, such as Vindoline and Tabersonin.
- Zhang, Chao,Zhan, Zhajun,Lei, Min,Hu, Lihong
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- Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
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Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.
- Singh, Anshu,Maji, Ankur,Joshi, Mayank,Choudhury, Angshuman R.,Ghosh, Kaushik
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- Synthesis of indoxylic acid esters by rhodium-catalyzed carbene n-h insertion and thermal cyclization
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Reaction between diethyl diazomalonate and a range of N-alkylanilines in the presence of a catalytic amount of rhodium(ii) acetate dimer afforded carbene N-H insertion to produce anilinomalonates in modest-to-good yields. Upon heating to a high temperatur
- Honey, Mark A.,Moody, Christopher J.
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- Design, synthesis and evaluation of novel bis-substituted aromatic amide dithiocarbamate derivatives as colchicine site tubulin polymerization inhibitors with potent anticancer activities
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As the continuation of our work on the development of tubulin inhibitors with potential anticancer activities, novel bis-substituted aromatic amide dithiocarbamate derivatives were designed by contacting bis-substituted aryl scaffolds (potential anti-tubulin fragments) with N-containing heterocycles (potential anti-tubulin fragments) in one hybrid using the anticancer dithioformate unit as the linker. The antiproliferative activity against three digestive tract tumor cells was evaluated and preliminary structure activity relationships were summarized. Among these compounds, compound 20q exhibited most potent antiproliferative activity against MGC-803, HCT-116, Kyse30 and Kyse450 cells with IC50 values of 0.084, 0.227, 0.069 and 0.078 μM, respectively. In further studies, compound 20q was identified as a novel tubulin inhibitor targeting the colchicine binding site. Compound 20q could inhibit the microtubule assembly and disrupt cytoskeleton in Kyse30 and Kyse450 cells. The results of molecular docking suggested that compound 20q could tightly bind into the colchicine binding site of tubulin by hydrogen bonds and hydrophobic interactions. Compound 20q dose-dependently inhibited the cell growth and colony formation, effectively arrested cells at the G2/M phase and induce mitochondrial apoptosis in Kyse30 and Kyse450 cells. In addition, Compound 20q could regulate the expression of G2/M phase and mitochondrial apoptosis related proteins. Collectively, compound 20q was here reported as a novel tubulin inhibitor with potential anticancer activities.
- Sun, Ya-Xin,Song, Jian,Kong, Li-Jun,Sha, Bei-Bei,Tian, Xin-Yi,Liu, Xiu-Juan,Hu, Tao,Chen, Ping,Zhang, Sai-Yang
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supporting information
(2021/12/31)
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- Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines
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Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.
- Wu, Di,Bu, Qingqing,Guo, Cheng,Dai, Bin,Liu, Ning
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- Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
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Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.
- Paudel, Keshav,Xu, Shi,Hietsoi, Oleksandr,Pandey, Bedraj,Onuh, Chuka,Ding, Keying
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supporting information
p. 418 - 426
(2021/02/01)
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- Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations
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Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.
- Louka, Anastasia,Kidonakis, Marios,Saridakis, Iakovos,Zantioti-Chatzouda, Elisavet-Maria,Stratakis, Manolis
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p. 3508 - 3514
(2020/06/02)
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- Chromium-Catalyzed Alkylation of Amines by Alcohols
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The alkylation of amines by alcohols is a broadly applicable, sustainable, and selective method for the synthesis of alkyl amines, which are important bulk and fine chemicals, pharmaceuticals, and agrochemicals. We show that Cr complexes can catalyze this C?N bond formation reaction. We synthesized and isolated 35 examples of alkylated amines, including 13 previously undisclosed products, and the use of amino alcohols as alkylating agents was demonstrated. The catalyst tolerates numerous functional groups, including hydrogenation-sensitive examples. Compared to many other alcohol-based amine alkylation methods, where a stoichiometric amount of base is required, our Cr-based catalyst system gives yields higher than 90 % for various alkyl amines with a catalytic amount of base. Our study indicates that Cr complexes can catalyze borrowing hydrogen or hydrogen autotransfer reactions and could thus be an alternative to Fe, Co, and Mn, or noble metals in (de)hydrogenation catalysis.
- Fertig, Robin,Irrgang, Torsten,Kallmeier, Fabian,Kempe, Rhett
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supporting information
p. 11789 - 11793
(2020/05/26)
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- Boron-Catalyzed N-Alkylation of Arylamines and Arylamides with Benzylic Alcohols
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A sustainable boron-based catalytic approach for chemoselective N-alkylation of primary and secondary aromatic amines and amides with primary, secondary, and tertiary benzylic alcohols has been presented. The metal-free protocol operates at low catalyst loading, tolerates several functional groups, and generates H2O as the sole byproduct. Preliminary mechanistic studies were performed to demonstrate the crucial role of boron catalyst for the activation of the intermediate dibenzyl ether and to identify the rate-determining step.
- Guru, Murali Mohan,Thorve, Pradip Ramdas,Maji, Biplab
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p. 806 - 819
(2020/01/02)
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- A microwave-assisted SmI2-catalyzed direct N-alkylation of anilines with alcohols
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A new protocol for the alkylation of aromatic amines has been described using alcohols in the presence of SmI2 as a catalyst with the generation of water as the sole byproduct. The reaction proceeds under MW conditions and selectively generates monoalkylated amines. This protocol features a broad substrate scope and good functional-group tolerance with moderate to high yields.
- Gour, Jitendra,Gatadi, Srikanth,Malasala, Satyaveni,Yaddanpudi, Madhavi Venkata,Nanduri, Srinivas
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p. 7488 - 7494
(2019/06/14)
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- An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature
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A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester were found to be very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the additional features of the current methodology. (Figure presented.).
- Chaudhary, Priyanka,Korde, Rishi,Gupta, Surabhi,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 556 - 561
(2017/11/13)
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- Application of a catalyst-free Domino Mannich/Friedel-Crafts alkylation reaction for the synthesis of novel tetrahydroquinolines of potential antitumor activity
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A useful and efficient method to construct diversely substituted 1,2,3,4-tetrahydroquinolines in good to excellent yields has been developed through a catalyst-free Domino Mannich and intramolecular Friedel-Crafts alkylation reactions of N-arylamines with
- Castillo, Juan-Carlos,Jiménez, Elizabeth,Portilla, Jaime,Insuasty, Braulio,Quiroga, Jairo,Moreno-Fuquen, Rodolfo,Kennedy, Alan R.,Abonia, Rodrigo
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p. 932 - 947
(2018/02/09)
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- Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts
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CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol. Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (105), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.
- Xi, Zi-Wei,Yang, Lei,Wang, Dan-Yan,Pu, Chao-Dan,Shen, Yong-Miao,Wu, Chuan-De,Peng, Xiao-Gang
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p. 11886 - 11895
(2018/09/25)
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- Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water
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Herein, an indazolyl-pyridinyl-triazole ligand was synthesized and its iridium complex supported on hydrotalcite was characterized via X-ray power diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray (EDX) spectroscopy and transmission electron microscopy (TEM). This new heterogeneous catalyst bearing the unsymmetrical indazolyl-pyridinyl-triazole ligand exhibits high catalytic activity in water. Both functionalized amines and imines were obtained from the challenging selective reaction of benzylamines with arylamines through transfer hydrogenation and dehydrogenation under clean conditions. In particular, it was observed that this catalyst system showed good recovery performance in water. Mechanistic studies showed that this transformation occurs via amine dehydrogenation, hydrolysis and condensation processes. The direct capture of the reaction intermediate provides sufficient proof for this process.
- Ge, Chenyang,Sang, Xinxin,Yao, Wei,Zhang, Liang,Wang, Dawei
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supporting information
p. 1805 - 1812
(2018/04/30)
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- Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines
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The catalytic system generated in situ from the tetranuclear Ru-H complex with a catechol ligand (1/L1) was found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to the coupling product with significant deuterium incorporation on CH2 (18% D). The most pronounced carbon isotope effect was observed on the α-carbon of the product isolated from the coupling reaction of 4-methoxybenzylamine (C(1) = 1.015(2)). A Hammett plot was constructed from measuring the rates of the coupling reaction of 4-methoxyaniline with a series of para-substituted benzylamines 4-X-C6H4CH2NH2 (X = OMe, Me, H, F, CF3) (ρ = -0.79 ± 0.1). A plausible mechanistic scheme has been proposed for the coupling reaction on the basis of these results. The catalytic coupling method provides an operationally simple and chemoselective synthesis of secondary amine products without using any reactive reagents or forming wasteful byproducts.
- Arachchige, Pandula T. Kirinde,Lee, Hanbin,Yi, Chae S.
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p. 4932 - 4947
(2018/05/08)
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- Selective reductive amination of aldehydes from nitro compounds catalyzed by molybdenum sulfide clusters
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Secondary amines are selectively obtained from low value starting materials using hydrogen and a non-noble metal-based catalyst. The reductive amination of aldehydes from nitroarenes or nitroalkanes is efficiently catalyzed by a well-defined diamino molybdenum sulfide cluster in a one-pot homogeneous reaction. The integrity of the molecular cluster catalyst is preserved along the process.
- Pedrajas,Sorribes,Junge,Beller,Llusar
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supporting information
p. 3764 - 3768
(2017/08/21)
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- Ruthenium-Catalyzed Selective Hydroboration of Nitriles and Imines
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Ruthenium-catalyzed hydroboration of nitriles and imines is attained using pinacolborane with unprecedented catalytic efficiency. Chemoselective hydroboration of nitriles over esters is also demonstrated. A simple [Ru(p-cymene)Cl2]2 complex (1) is used as a catalyst precursor, which upon reaction with pinacolborane in situ generates the monohydrido-bridged complex [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] 2. Further oxidative addition of pinacolborane to intermediate 2 leading to the formation of mononuclear ruthenium hydride species is suggested. Mass spectral analysis of the reaction mixture and independent experiments with phosphine-ligated ruthenium complexes indicated the involvement of mononuclear ruthenium intermediates in the catalytic cycle. Consecutive intramolecular 1,3-hydride transfers from the ruthenium center to coordinated nitrile and boronate imine ligands, leading to the reduction and resulting in the formation of diboronate amines, are proposed as a plausible reaction mechanism.
- Kaithal, Akash,Chatterjee, Basujit,Gunanathan, Chidambaram
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p. 11153 - 11163
(2016/11/28)
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- Alanine triazole iridium-catalyzed C–N bond formation through borrowing hydrogen strategy
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An efficient synthesis of secondary amines has been described through alanine triazole iridium-catalyzed C–N bond formation of an aromatic amine and an alkyl amine using the borrowing hydrogen strategy. In addition, it was observed that alanine triazole iridium is also an efficient catalyst to promote C–N bond formation of an aromatic amine and alcohols with good to excellent yields.
- Yu, Xiaoli,Zhao, Ranran,Wan, Huida,Yang, Yongchun,Wang, Dawei
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supporting information
p. 4588 - 4591
(2016/09/23)
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- Fe3O4@SiO2/EDAC-Pd(0) as a novel and efficient inorganic/organic magnetic composite: Sustainable catalyst for the benzylic C-H bond oxidation and reductive amination under mild conditions
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A facile and novel methodology has been reported for the synthesis of Pd(0) nanoparticles onto ethylene diamine functionalized inorganic/organic magnetic composite [Fe3O4@SiO2/EDAC-Pd(0)]. The amine functionalized inorganic/organic substrate proved to be an efficient host for the immobilization of palladium nanoparticles giving a highly stable, water dispersible, active and yet magnetically recoverable heterogeneous catalyst. The synthesized catalyst displayed remarkable activity towards the selective C-H bond oxidation using TBHP and reductive amination of aldehydes with nitroarenes using atom efficient molecular hydrogen in green solvents, and could be reused efficiently upto 6 consecutive runs. The novel catalyst is characterized by FT-IR, TGA, XRD, SEM, HRTEM, EDX, ICP-AES, XPS and VSM techniques. Because of the magnetic nature of the catalyst, it can be retrieved using an external magnet, which eliminates the obligation of catalyst filtration after completion of the reaction, thus making it an eco-friendly and economical catalyst to perform the organic transformations.
- Bhardwaj, Madhvi,Sharma, Harsha,Paul, Satya,Clark, James H.
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p. 4952 - 4961
(2016/07/06)
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- Copper N-Heterocyclic Carbene: A Catalyst for Aerobic Oxidation or Reduction Reactions
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Copper N-heterocyclic carbene complexes can be readily used as catalysts for both aerobic oxidation of alcohols to aldehydes and reduction of imines to amines. Our methodology is universal for aromatic substrates and shows versatile tolerance to potential cascade reactions. A one-pot tandem synthetic strategy could afford useful imines and secondary amines via an oxidation-reduction strategy.
- Zhan, Le-Wu,Han, Lei,Xing, Ping,Jiang, Biao
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supporting information
p. 5990 - 5993
(2016/01/09)
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- Ionic liquid coated sulfonated carbon/silica composites: Novel heterogeneous catalysts for organic syntheses in water
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Ionic liquid coated sulfonic acid functionalized amorphous carbon/silica composites derived from a starch-glucose mixture were developed and their catalytic activities were evaluated for Knoevenagel condensation, reductive amination of aldehydes and ketones, and for Michael addition of indole to α,β-unsaturated ketones in aqueous medium. The catalyst prepared from starch-glucose mixture (3:1) [CSC-Star-Glu-IL2] showed the highest activity in water. The catalysts were characterized by FTIR, TGA, elemental analysis, and the most active was further characterized by XRD, SEM and TEM.
- Gupta, Princy,Kour, Manmeet,Paul, Satya,Clark, James H.
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p. 7461 - 7470
(2014/02/14)
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- Efficient and chemoselective direct reductive amination of aromatic aldehydes catalyzed by oxo-rhenium complexes containing heterocyclic ligands
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This work describes the catalytic activity of 17 oxo-rhenium complexes containing heterocyclic ligands in the direct reductive amination of 4-nitrobenzaldehyde with 4-chloroaniline, using phenylsilane as reducing agent. In general, all of the catalysts tested gave excellent yields of the secondary amine, although, the best result was obtained with the catalytic system PhSiH3/ReOBr2(Hhmpbta)(PPh3) (2.5 mol %). This system was also applied to the synthesis of a large variety of secondary amines in good to excellent yields and tertiary amines in moderate yields, with tolerance of different functional groups.
- Bernardo, Joana R.,Sousa, Sara C.A.,Florindo, Pedro R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.
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p. 9145 - 9154
(2013/09/24)
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- In(OTf)3 catalyzed N-benzylation of amines utilizing benzyl alcohols in water
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An In(OTf)3-catalyzed N-benzylation of amines utilizing benzyl alcohols through direct C-O bond activation has been reported. The reaction was performed in water without any base, additive, ligand or inert gas protection to afford the chem-selective mono- or bis-alkylated aromatic amines in good to excellent yields.
- Yang, Jin-Ming,Jiang, Ran,Wu, Lin,Xu, Xiao-Ping,Wang, Shun-Yi,Ji, Shun-Jun
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p. 7988 - 7994
(2013/08/23)
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- Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols
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A series of HSO4- functionalized ILs was synthesized and used as efficient, green, and metal-free catalysts for benzylation. Notably, the catalytic system has wide substrate scopes and the ionic liquid catalysts were applied to investigate three different types of nucleophiles to give the desired benzylation products with moderate to excellent yields.
- Chu, Xue-Qiang,Jiang, Ran,Fang, Yi,Gu, Zheng-Yang,Meng, Hua,Wang, Shun-Yi,Ji, Shun-Jun
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supporting information
p. 1166 - 1174
(2013/02/25)
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- Gallium(III) triflate catalyzed direct reductive amination of aldehydes
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Direct hydroamination of aldehydes and ketones provides one-step entry into desired α-aminoalkane derivatives which are important synthons for many biologically active molecules. The reductive amination of aldehydes in the presence of silanes has been eff
- Surya Prakash,Do, Clement,Mathew, Thomas,Olah, George A.
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experimental part
p. 111 - 117
(2010/11/05)
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- Efficient and highly chemoselective direct reductive animation of aldehydes using the system silane/oxorhenium complexes
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This work reports a novel method for direct reductive amination of aldehydes with silanes catalyzed by several high-valent oxorhenium(V) and oxorhenium (VII) complexes. The catalytic system PhSiH3/ReIO 2(PPh3)2 (2.5mol%) was very efficient for the synthesis of secondary amines and highly chemoselective, tolerating a wide range of functional groups such as -NO2, -CF3, -SO 2R, -CO2R, -F, -Cl, -Br, -I, -CN, -OH, -OCH3, -SCH3, NCOR, and double bonds. This novel method was also employed in the synthesis of tertiary amines with moderate yields.
- Sousa, Sara C. A.,Fernandes, Ana C.
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experimental part
p. 2218 - 2226
(2010/11/05)
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- New heteroaromatic azo compounds based on pyridine, isoxazole, and benzothiazole for efficient and highly selective amidation and mono-N-benzylation of amines under Mitsunobu conditions
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4,4′-Azopyridine (2c) is used in conjunction with triphenylphosphine for the efficient conversion of carboxylic acids into amides via Mitsunobu reaction with primary and secondary aliphatic and aromatic amines. The highly selective amidation of only primary aromatic amines with new heterogeneous azo compounds based on benzothiazole 2d and isoxazole 2e is also described. These azo compounds 2c-2e can also be applied for selective mono-N-benzylation of primary aromatic amines. The solid side product heteroaromatic hydrazines obtained under the developed Mitsunobu conditions are easily separated by simple filtration and can be reoxidized to azo compounds for further use.
- Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush
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experimental part
p. 923 - 934
(2010/10/01)
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- Transfer hydrogenation of imines with ammonia-borane: A concerted double-hydrogen-transfer reaction
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(Chemical Equation Presented) Direct transfer hydrogenation of imines was observed with ammonia-borane, which proceeded under mild conditions without the help of a catalyst. The results of deuterium kinetic isotope effects, Hammett correlations, and DFT calculations all support a concerted double-hydrogen- transfer mechanism (see scheme).
- Yang, Xianghua,Zhao, Lili,Fox, Thomas,Wang, Zhi-Xiang,Berke, Heinz
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supporting information; experimental part
p. 2058 - 2062
(2010/06/20)
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- 11-Phenyl-[b,e]-dibenzazepine compounds: Novel antitumor agents
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A series of 11-phenyl-[b,e]-dibenzazepine compounds were synthesized and shown to be inhibitors of tumor cell proliferation with IC50 values ranging from submicromolar to micromolar concentrations. Flow cytometric analyses of several active com
- Al-Qawasmeh, Raed A.,Lee, Yoon,Cao, Ming-Yu,Gu, Xiaoping,Viau, Stephane,Lightfoot, Jeff,Wright, Jim A.,Young, Aiping H.
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scheme or table
p. 104 - 107
(2009/04/16)
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- Reductive amination of carbonyl compounds using NaBH4 in a Br?nsted acidic ionic liquid
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Reductive amination of carbonyl compounds using sodium borohydride is conducted in the Br?nsted acidic ionic liquid, 1-methyl imidazolium tetrafluoroborate ([HMIm][BF4]). The ionic liquid plays the dual role of solvent as well as catalyst for efficient conversion of aldehydes and ketones to amines in excellent yields without the formation of side products.
- Reddy, P. Srinivasa,Kanjilal, Sanjit,Sunitha,Prasad, Rachapudi B.N.
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p. 8807 - 8810
(2008/03/18)
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- Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile
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The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.
- Choi, Jin Heui,Lee, Byung Choon,Lee, Hai Whang,Lee, Ikchoon
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p. 1277 - 1281
(2007/10/03)
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- Electroreduction of Some Azomethine Compounds at Copper and Copper Amalgam Cathodes
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The electrochemical reducibility of some azomethine compounds derived from aniline, its derivatives, 2-aminopyridine, and 2-aminobenzothiazole and aromatic aldehydes at copper and copper amalgam cathodes in acid medium has been investigated.It is found that reducibility of the compounds increases with increase in hydrogen overvoltage of the cathode and decrease in current density.Furthermore the reducibility of the azomethine compounds possessing non-hetero aromatic amine moiety is higher than that of compounds possessing heteroaromatic amine moiety.
- Awad, A.,El-Cheikh, F.,Mourad, R.
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p. 176 - 178
(2007/10/02)
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