- Bis(cyclohexanone) oxalyldihydrazone/copper(II) oxide - A novel and efficient catalytic system for ullmann-type C-N coupling in pure water
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Animations of aryl halides were conducted under fast copper- bis(cyclohexanone) oxalyldihydrazone catalysis in pure water with both temperature-controlled microwave heating and traditional heating. With a reaction time of five minutes under microwave heating at 130 °C or at reflux for 10 hours, both electron-rich and electron-deficient aryl halides reacted with various amines to provide fair to good yields of the corresponding anilines. Georg Thieme Verlag Stuttgart.
- Zhu, Xinhai,Ma, Yan,Su, Li,Song, Huacan,Chen, Gong,Liang, Dacheng,Wan, Yiqian
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- Rational Optimization of Lewis-Acid Catalysts for Direct Alcohol Amination, Part 2 – Titanium Triflimide as New Active Catalyst
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The reactivity of a new titanium triflimide salt (see Part 1) was investigated for the direct amination of alcohols. The combination of this new Lewis acid with pyridine-based ligands allowed a significant increase of activity. The scope of the reaction was increased compared to other Lewis-acid-based protocols. Finally, mechanistic insights based on EPR spectroscopy and DFT calculations are provided.
- Payard, Pierre-Adrien,Finidori, Céline,Guichard, Laurélia,Cartigny, Damien,Corbet, Matthieu,Khrouz, Lhoussain,Bonneviot, Laurent,Wischert, Raphael,Grimaud, Laurence,Pera-Titus, Marc
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- Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols
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The implementation of inexpensive, Earth-abundant metals in typical noble-metal-mediated chemistry is a major goal in homogeneous catalysis. A sustainable or green reaction that has received a lot of attention in recent years and is preferentially catalyzed by Ir or Ru complexes is the alkylation of amines by alcohols. It is based on the borrowing hydrogen or hydrogen autotransfer concept. Herein, we report on the Co-catalyzed alkylation of aromatic amines by alcohols. The reaction proceeds under mild conditions, and selectively generates monoalkylated amines. The observed selectivity allows the synthesis of unsymmetrically substituted diamines. A novel Co complex stabilized by a PN5P ligand catalyzes the reactions most efficiently. Sustainable C-N bond formation: An easily accessible Co complex efficiently catalyzes the alkylation of aromatic amines by alcohols. The mild reaction conditions permit the use of sensitive functional groups (I, Br) and the observed selective monoalkylation allows the synthesis of unsymmetrically alkylated diamines.
- R?sler, Sina,Ertl, Michael,Irrgang, Torsten,Kempe, Rhett
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- Structure-activity relationship study of homoallylamines and related derivatives acting as antifungal agents
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The synthesis, in vitro evaluation, and structure-activity relationship studies of homoallylamines and related derivatives acting as antifungal agents are reported. Among them, compounds N-(4-bromophenyl)-N-(2-furylmethyl)amine and N-(4-chlorophenyl)-N-(2
- Suvire, Fernando D.,Sortino, Maximiliano,Kouznetsov, Vladimir V.,Vargas M, Leonor Y.,Zacchino, Susana A.,Cruz, Uriel Mora,Enriz, Ricardo D.
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Read Online
- Tungsten-Catalyzed Direct N-Alkylation of Anilines with Alcohols
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The implementation of non-noble metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of non-noble metal catalysts. Herein, we report a tungsten-catalyzed N-alkylation reaction of anilines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.
- Lan, Xiao-Bing,Ye, Zongren,Yang, Chenhui,Li, Weikang,Liu, Jiahao,Huang, Ming,Liu, Yan,Ke, Zhuofeng
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p. 860 - 865
(2021/01/18)
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- Mimicking transition metals in borrowing hydrogen from alcohols
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Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to anin situgenerated imine is the hallmark of a transition metal mediated catalyticN-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established. Herein, we demonstrate that a phenalenyl ligand can imitate the role of transition metals in storing and transferring hydrogen molecules leading to borrowing hydrogen mediated alkylation of anilines by alcohols including a wide range of substrate scope. A close inspection of the mechanistic pathway by characterizing several intermediates through various spectroscopic techniques, deuterium labelling experiments, and DFT study concluded that the phenalenyl radical based backbone sequentially adds H+, H˙ and an electron through a dearomatization process which are subsequently used as reducing equivalents to the C-N double bond in a catalytic fashion.
- Banik, Ananya,Ahmed, Jasimuddin,Sil, Swagata,Mandal, Swadhin K.
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p. 8353 - 8361
(2021/07/02)
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- Convenient and Reusable Manganese-Based Nanocatalyst for Amination of Alcohols
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The development of new sustainable nanocatalytic systems for green chemical synthesis is a growing area in chemical science. Herein, a reusable heterogeneous N-doped graphene-based manganese nanocatalyst (Mn@NrGO) for selective N-alkylation of amines with alcohols is described. Mechanistic studies illustrate that the catalytic reaction follows a domino dehydrogenation-condensation-hydrogenation sequence of alcohols and amines with the formation of water as the sole by-product. The scope of the reaction is extended to the synthesis of pharmaceutically important N-alkylated amine intermediates. The heterogeneous nature of the catalyst made it easy to separate for long-term performance, and the recycling study revealed that the catalyst was robust and retained its activity after several recycling experiments.
- Subaramanian, Murugan,Ramar, Palmurukan M.,Sivakumar, Ganesan,Kadam, Ravishankar G.,Petr, Martin,Zboril, Radek,Gawande, Manoj B.,Balaraman, Ekambaram
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p. 4334 - 4341
(2021/08/25)
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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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- Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation
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Diimine (HN═NH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.
- Chen, Guoliang,He, Xiaoyan,Huang, Gang,Lu, Xiuhong,Wang, Jincheng,Yang, Zhenjiao,Zhang, Yongsheng,Zhang, Zeng
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p. 17696 - 17709
(2021/12/09)
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- Base-mediated cascade amidination/: N -alkylation of amines by alcohols
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A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.
- Hu, Mao-Lin,Jia, Xiaofei,Liang, Zuyu,Lu, Fenghong,Zhang, Chunyan,Zhang, Guoying
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supporting information
p. 10489 - 10492
(2020/10/02)
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- Alkylation synthesis method of in-situ catalytic alcohol (by machine translation)
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The method comprises VIB metal complexes, an auxiliary ligand and a base as a catalytic reaction system, wherein the alcohol serves as an alkylating agent, and the nucleophilic substrate is subjected to in-situ catalytic alkylation reaction in a solvent and an inert gas atmosphere. The catalytic system has a wide application range on a substrate, can catalyze the synthesis of C-N and C-C bond compounds of different structures under mild conditions, and can green synthesize a series of valuable N - alkylation and C - alkylation compounds. (by machine translation)
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Paragraph 0039-0041; 0048-0050
(2020/11/01)
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- Base-Mediated Amination of Alcohols Using Amidines
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Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.
- Chen, Jianbin,Fang, Yanchen,Jia, Xiaofei,Jiang, Shaohua,Li, Zehua,Liang, Zuyu,Lu, Fenghong,Qi, Shuo,Ren, Chaoyu,Yu, Shuangming,Zhang, Chunyan,Zhang, Guoying,Zhang, Sheng
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p. 7728 - 7738
(2020/07/15)
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- A Highly Active PN3 Manganese Pincer Complex Performing N-Alkylation of Amines under Mild Conditions
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A highly active Mn(I) catalyst based on a nonsymmetric PN3-ligand scaffold for the N-alkylation of amines with alcohols utilizing the borrowing hydrogen methodology is reported. A broad range of anilines and the more challenging aliphatic amines were alkylated with primary and secondary alcohols. Moreover, the combination of low catalyst loadings and mild reaction conditions provides high efficiency for this atom-economic transformation.
- Homberg, Leonard,Roller, Alexander,Hultzsch, Kai C.
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supporting information
(2019/05/07)
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- Unmodified Fe3O4 nanostructure promoted with external magnetic field: safe, magnetically recoverable, and efficient nanocatalyst for N- and C-alkylation reactions in green conditions
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Transition metal compounds have emerged as suitable catalysts for organic reactions. Magnetic compounds as soft Lewis acids can be used as catalysts for organic reactions. In this report, the Fe3O4 nanostructures were obtained from Fe2+ and Fe3+-salts, under an external magnetic field (EMF) without any protective agent. The X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy tools were used to characterize these magnetic compounds. The two-dimensional (2-D, it showed nanometric size in the two dimensions, nanorod structure) Fe3O4 compound showed high catalytic activity and stability in N- and C-alkylation reactions. A diverse range of N- and C-alkylation products were obtained in moderate to high yield under green and mild conditions in air. Also the N- and C-alkylation products can be obtained with different selectivity and yield by exposure reactions with EMF. Results of alkylation reactions showed that the presence of Fe(II) and Fe(III) species on the surface of magnetic catalysts (phase structure of magnetic compounds) are essential as very cheap active sites. Also, morphology of magnetic catalysts had influence on their catalytic performances. After the reaction, the catalyst/product(s) separation could be easily achieved with an external magnet and more than 95% of catalyst could be recovered. The catalyst was reused at least four times without any loss of its high catalytic activity for N- and C-alkylation reactions.
- Rafiee, Ezzat,Joshaghani, Mohammad,Abadi, Parvaneh Ghaderi-Shekhi
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p. 2503 - 2522
(2018/01/04)
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- Manganese-Catalyzed and Base-Switchable Synthesis of Amines or Imines via Borrowing Hydrogen or Dehydrogenative Condensation
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The use of earth-abundant transition metals as a noble metal replacement in catalysis is especially interesting if different catalytic reactivity is observed. We report, here, on the selective manganese-catalyzed base-switchable synthesis of N-alkylated amines or imines. In both reactions, borrowing hydrogen/hydrogen autotransfer (N-alkyl amine formation) or dehydrogenative condensation (imine formation), we start from the same amines and alcohols and use the same Mn precatalyst. The key is the presence of a potassium base to prefer N-alkylation and a sodium base to permit imine formation. Both bases react with the manganese hydride via deprotonation. The potassium manganate hydride reacts about 40 times faster with an imine to give the corresponding amine than the sodium manganate hydride. The selectivity seems unique for manganese complexes. We observe a broad scope with a complete product overlap, all amine alcohol combinations can be converted into an N-alkyl amine or an imine, and a good functional group tolerance.
- Fertig, Robin,Irrgang, Torsten,Freitag, Frederik,Zander, Judith,Kempe, Rhett
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p. 8525 - 8530
(2018/09/06)
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- An Efficient Homogenized Ruthenium(II) Pincer Complex for N-Monoalkylation of Amines with Alcohols
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An ionic 2,6-bis(imidazo[1,2-α]pyridin-2-yl)pyridine-based N^N^N pincer ruthenium(II) complex exhibited high efficiency in the C–N bond formation between amines and alcohols by the “borrowing hydrogen” (BH) or “hydrogen autotransfer” (HA) concept. The synthetic protocol selectively generated monoalkylated amines without formation of tertiary amines during the reaction. The unique selectivity enabled the formation of symmetrically and asymmetrically substituted diamines. This methodology features several advantages including a low catalyst loading (as low as 0.5 mol-%), a short reaction time (as short as 2 h), and excellent N-monoalkylation selectivity.
- Yang, Fa-Liu,Wang, Ying-Hui,Ni, Yong-Feng,Gao, Xiang,Song, Bing,Zhu, Xinju,Hao, Xin-Qi
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p. 3481 - 3486
(2017/07/04)
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- Transition metal free catalytic hydroboration of aldehydes and aldimines by amidinato silane
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The transition metal free catalytic hydroboration of aldehydes and ketones is very limited and has not been reported with a well-defined silicon(iv) compound. Therefore, we chose to evaluate the previously reported silicon(iv) hydride [PhC(NtBu)2SiHCl2], (1) as a single component catalyst and found that it catalyzes the reductive hydroboration of a range of aldehydes with pinacolborane (HBpin) under ambient conditions. In addition, compound 1 can catalyze imine hydroboration. DFT calculation was carried out to understand the mechanism.
- Bisai, Milan Kumar,Pahar, Sanjukta,Das, Tamal,Vanka, Kumar,Sen, Sakya S.
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p. 2420 - 2424
(2017/03/08)
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- A process for preparing amine compound using carbon-supported cobalt-rhodium nanoparticel catalyzed hydrogen-free recuctive amination
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The present invention relates to hydrogen-free reductive amination of an aldehyde and/or ketone and an amine and/or nitroarene using cobalt-rhodium heterometal nanoparticles supported on carbon as a non-homogeneous catalyst. According to the present invention, it is possible to carry out amination under significantly lower pressure as compared to the reductive amination carried out in the presence of a conventional rhodium or ruthenium catalyst. In addition, there is no need for using an additional ligand, acid or base. Further, it is possible to use water generated in a reaction system by a water-gas shift reaction as a hydrogen source with no use of an external hydrogen source, and thus to use a solvent without purification. Thus, it is possible to simplify the reaction procedure. The catalyst system according to the present invention provides a simple method for preparing secondary and tertiary amines from various aldehydes and amines.
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Paragraph 0066; 0070; 0074
(2017/04/25)
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- Hydrogen-Free Cobalt-Rhodium Heterobimetallic Nanoparticle-Catalyzed Reductive Amination of Aldehydes and Ketones with Amines and Nitroarenes in the Presence of Carbon Monoxide and Water
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Cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive amination of aldehydes and ketones with amines in the presence of 5 atm carbon monoxide without an external hydrogen source has been developed. Water added and generated in situ produces hydrogen via a water-gas-shift reaction. The reaction can be extended to the tandem reduction of aldehydes and ketones with nitroarenes. The catalytic system is stable under the reaction conditions and could be reused eight times without losing any catalytic activity. (Chemical Equation Presented).
- Park, Jang Won,Chung, Young Keun
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p. 4846 - 4850
(2015/08/18)
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- One-pot synthesis of secondary amines from alcohols and nitroarenes on TiO2 loaded with Pd nanoparticles under UV irradiation
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Photoirradiation (λ > 300 nm) of TiO2 loaded with Pd nanoparticles (2 wt%, ca. 5 nm diameter) in water containing benzyl alcohol and nitrobenzene at room temperature successfully produces the corresponding secondary amine (N-benzylaniline) with 96% yield. This is achieved via three consecutive catalytic reactions: (i) photocatalytic oxidation of alcohol (aldehyde formation) and reduction of nitrobenzene (aniline formation); (ii) catalytic condensation of the formed aldehyde with aniline on the TiO2 surface (imine formation); and, (iii) photocatalytic hydrogenation of the formed imine (secondary amine formation). This catalytic system successfully produces several kinds of secondary amines, even those containing reducible substituents such as -CN, -COOH, or -CHO with >76% yields.
- Selvam, Kaliyamoorthy,Sakamoto, Hirokatsu,Shiraishi, Yasuhiro,Hirai, Takayuki
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p. 2467 - 2473
(2015/04/14)
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- Ag nanoparticles on mixed Al2O3-Ga2O 3 supports as catalysts for the N-alkylation of amines with alcohols
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The combination of AgNO3 with NaH results in Ag nanoparticles that can selectively perform alcohol aminations under mild reaction conditions (110 C). NaH not only serves as a reducing agent for the Ag salt, but also activates the alcohol for dehydrogenation to the corresponding ketone/aldehyde. The stability of the particles can be improved by immobilizing them onto mixed Al2O3-Ga2O3 supports; the combination of Ga and Al provides materials with stronger Lewis acidic sites compared to pure alumina or gallium oxide supports. This leads to catalysts with enhanced activities, without the necessity of adding external Lewis acids. Detailed TEM characterization also reveals a close interaction between the Ag NPs and the gallium oxide phase. The obtained catalysts are recyclable and show activity for the alcohol amination using a variety of aliphatic and aromatic amines under mild conditions.
- Geukens, Inge,Vermoortele, Frederik,Meledina, Maria,Turner, Stuart,Van Tendeloo, Gustaaf,De Vos, Dirk E.
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p. 373 - 379
(2013/11/19)
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- A catalyst system, copper/ N -methoxy-1 H -pyrrole-2-carboxamide, for the synthesis of phenothiazines in poly(ethylene glycol)
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A copper/N-methoxy-1H-pyrrole-2-carboxamide catalyst system has been established for the preparation of phenothiazines in good yields by two routes, starting from 2-iodoanilines and 2-bromobenzenethiol and from aryl ortho-dihalides and o-aminobenzenethiols, by conducting the reaction at 90 °C in poly(ethylene glycol)-100 (PEG-100). In addition, the catalyst system was useful for promoting direct arylation of various aryl amines, aliphatic amines, and aqueous ammonia. The simple experimental operation, low loading of catalyst system together with the use of green solvent, makes it attractive for the versatile syntheses of phenothiazines and various amines.
- Huang, Manna,Hou, Jianying,Yang, Ruiqiao,Zhang, Liting,Zhu, Xinhai,Wan, Yiqian
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supporting information
p. 3356 - 3364
(2015/02/02)
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- Synthesis and anticholinesterase activity of fumaramide derivatives
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A series of fumaramide derivatives were synthesized from substituted benzanilines and their cholinesterase inhibitory activity was assayed according to Ellman's method using galanthamine-HBr as the reference compound. Most of the fumaramide compounds showed inhibitory activity of both cholinesterase enzymes. Compounds 29 (IC50 = 0.14 μM) and 30 (IC50 = 16.50 μM) were found to be the most active inhibitors on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes, respectively. Molecular docking studies were performed with Surflex-Dock programme to provide the possible interactions between compounds and enzymes. A Lineweaver-Burk plot and molecular modelling studies showed that fumaramide compounds targeted both the catalytic anionic site and the peripheral anionic site of AChE. It was revealed that the nature of α,β-unsaturated 1,4-diketone moiety in fumaramide compounds brought about useful and efficient modification especially on AChE inhibition.
- Yerdelen, Kadir Ozden,Gul, Halise Inci
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p. 4920 - 4929
(2013/09/23)
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- Tris(acetylacetonato)rhodium(III)-catalyzed α-alkylation of ketones, β-alkylation of secondary alcohols and alkylation of amines with primary alcohols
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The tris(acetylacetonato)rhodium(III) catalyst is shown to be a versatile catalyst in the presence of DABCO (1,4-diazabicyclo[2.2.2]octane) as ligand for the α-alkylation of ketones followed by transfer hydrogenation, for the one-pot β-alkylation of secondary alcohols with primary alcohols and for the alkylation of aromatic amines in the presence of an inorganic base in toluene. Copyright
- Satyanarayana, Ponnam,Reddy, Ganapam Manohar,Maheswaran, Hariharasharma,Kantam, Mannepalli Lakshmi
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supporting information
p. 1859 - 1867
(2013/07/19)
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- Palladium supported on magnetic nanoparticles as recoverable catalyst for one-pot reductive amination of aldehydes with nitroarenes under ambient conditions
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A high-performance palladium-based catalyst has been prepared by the co-precipitation method. The catalyst was characterized by TEM, XRD, VSM and ICP. It was found that the catalyst showed a high activity for the one-pot direct reductive amination of aldehydes with nitroarenes in the presence of molecular hydrogen in ethanol, even at room temperature. Furthermore, the catalyst was easily recovered by applying an external magnet and reused for eight cycles without significant loss of activity.
- Wei, Shuoyun,Dong, Zhengping,Ma, Zongyan,Sun, Jian,Ma, Jiantai
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- One-pot synthesis of aniline derivatives from nitroarenes under mild conditions promoted by a recyclable polymer-supported palladium catalyst
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This work describes the one-pot direct reductive amination of carbonyl compounds with nitroarenes promoted by a polymer supported palladium catalyst, in the presence of molecular hydrogen as the reductant. This methodology is applicable, with slight differences, to both aliphatic and aromatic aldehydes. The operational simplicity, the mild reaction conditions, the high yields and the good recyclability of the supported catalyst are major advantages of this method. TEM observations of the catalyst showed that the active species are palladium nanoparticles having a size distribution centered at 5 nm within the polymeric support.
- Dell'Anna, Maria Michela,Mastrorilli, Piero,Rizzuti, Antonino,Leonelli, Cristina
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scheme or table
p. 134 - 140
(2012/03/27)
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- N2,N2′-disubstituted oxalic acid bishydrazides: Novel ligands for copper-catalyzed Ci£N coupling reactions in water
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A series of N2,N2′-disubstituted oxalic acid bishydrazides were synthesized. Some, for example, N2,N 2′-di-1-(4-methoxyphenyl)-ethanyloxylic-(bishydrazide), are novel and effective ligands for copper-catalyzed Ullmann-type Ci£N coupling reaction in water. A variety of amines could be effectively N-arylated with aryl halides under both microwave irradiation and conventional heating (even at 30 °C) with good to excellent yields.
- Meng, Fei,Wang, Chenxia,Xie, Jianwei,Zhu, Xinhai,Wan, Yiqian
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experimental part
p. 341 - 347
(2012/05/04)
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