- Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
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We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
- Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
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supporting information
p. 9419 - 9424
(2021/11/30)
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- Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
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Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.
- Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
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supporting information
(2020/09/02)
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- Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide
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Recent developments in the chemistry of C-N bond formation and the synthesis of anilines have allowed for the use of first-row transition metals to catalyze these transformations. Much of the progress in this area has been driven by comprehensive screening for privileged/tailored ligands, which can be costly and not readily available in a research laboratory setting. In this communication we report a protocol in which simple nickel salts catalyze the C-N cross-coupling reaction between (hetero)aryl bromides and iodides with lithium bis(trimethylsilyl)amide without the need for any additive ligand. This method is amenable to low nickel catalyst loadings (1%) as well as gram-scale reactions. Because of the good functional group tolerance and compatibility with heterocyclic moieties, this method is useful for academic laboratory settings where access to tailored ligands and noble-metal catalysts could be challenging.
- Martinez, Gabriel Espinosa,Nugent, Joseph W.,Fout, Alison R.
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supporting information
p. 2941 - 2944
(2018/09/21)
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- AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0257
(2018/03/25)
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- Copper mediated C-H amination with oximes: En route to primary anilines
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Here we report an efficient Cu(i)-mediated C-H amination reaction with oximes as amino donors to introduce NH2 groups directly. Various strongly coordinating heterocycles including quinoline, pyrimidine, pyrazine, pyrazole and triazole were tolerated well. The potential utility was further demonstrated in a late-stage modification of telmisartan (an antagonist for the angiotensin II receptor).
- Xu, Lin-Lin,Wang, Xing,Ma, Biao,Yin, Ming-Xing,Lin, Hai-Xia,Dai, Hui-Xiong,Yu, Jin-Quan
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p. 5160 - 5164
(2018/06/21)
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- Non-deprotonative primary and secondary amination of (hetero)arylmetals
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Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.
- Zhou, Zhe,Ma, Zhiwei,Behnke, Nicole Erin,Gao, Hongyin,Kürti, László
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supporting information
p. 115 - 118
(2017/05/16)
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- Highly chemoselective reduction of azides to amines by Fe(0) nanoparticles in water at room temperature
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A highly chemoselective reduction of aryl, heteroaryl, acyl and sulfonyl azides to the corresponding amines has been achieved by Fe(0) nanoparticles in water at room temperature in the absence of external hydride source. Several readily reducible functionalities including alkene, alkyne, S-S linkage, OTBDMS remain unaffected during reduction.
- Panja, Subir,kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
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supporting information
p. 3457 - 3460
(2017/08/10)
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- Discovery of N-(Naphthalen-1-yl)-N′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers
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A class of N-(naphthalen-1-yl)-N′-alkyl oxalamides have been proven to be powerful ligands, making a coupling reaction of (hetero)aryl iodides with primary amines proceed at 50 °C with only 0.01 mol % of Cu2O and ligand as well as a coupling reaction of (hetero)aryl bromides with primary amines and ammonia at 80 °C with only 0.1 mol % of Cu2O and ligand. A wide range of coupling partners work well under these conditions, thereby providing an easy to operate method for preparing (hetero)aryl amines.
- Gao, Jie,Bhunia, Subhajit,Wang, Kailiang,Gan, Lu,Xia, Shanghua,Ma, Dawei
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supporting information
p. 2809 - 2812
(2017/06/07)
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- A Metal and Base-Free Chemoselective Primary Amination of Boronic Acids Using Cyanamidyl/Arylcyanamidyl Radical as Aminating Species: Synthesis and Mechanistic Studies by Density Functional Theory
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An efficient, metal and base-free, chemoselective synthesis of aryl-, heteroaryl-, and alkyl primary amines from the corresponding boronic acids has been achieved at ambient temperature mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) and N-bromosuccinimide (NBS) using cyanamidyl/arylcyanamidyl radicals as the aminating species. The primary amine compounds were initially obtained as their corresponding ammonium trifluoroacetate salts which, on treatment with aq NaOH, provide the free amines. Finally, the primary amines were isolated through column chromatography over silica-gel using hexane-EtOAc solvent system as the eluent. The reactions are sufficiently fast, completing within 1 h. Quantum chemical calculations in combination with experimental observations validate that the ipso amination of substituted boronic acids involves the formation of cyanamidyl/arylcyanamidyl radical, followed by regiospecific interaction of its nitrile-N center with boron atom of the boronic acids, leading to chemoselective primary amination.
- Chatterjee, Nachiketa,Arfeen, Minhajul,Bharatam, Prasad V.,Goswami, Avijit
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p. 5120 - 5127
(2016/07/06)
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- Amination-Oxidation Strategy for the Copper-Catalyzed Synthesis of Monoarylamines
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A novel approach for the synthesis of monoarylamines from aryl halides is presented. This method employs an inexpensive, nontoxic metal source (copper) and incorporates a stable ammonia surrogate (α-amino acids), obviating the need for special experimental setup or handling of ammonia reagents. This process, which is proposed to proceed via an amination-oxidation sequence, selectively promotes the transformation of a range of aryl and heteroaryl iodides as well as bromides to the corresponding monoarylamines.
- Thomas, Christopher,Wu, Marvin,Billingsley, Kelvin L.
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p. 330 - 335
(2016/01/15)
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- Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia
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A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.
- Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 5934 - 5937
(2015/12/11)
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- Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite
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A direct and eco-friendly nitration methodology to synthesize 3-nitroquinoline N-oxides from quinoline N-oxides using tert-butyl nitrite as both the nitro source and oxidant has been developed. Although this reaction undergoes a free radical process, it exhibits high regioselectivity and can be smoothly scaled up to gram scale. This journal is
- Zhao, Jingjing,Li, Pan,Xia, Chungu,Li, Fuwei
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p. 32835 - 32838
(2015/04/27)
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- Nickel-catalyzed monoarylation of ammonia
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Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.
- Borzenko, Andrey,Rotta-Loria, Nicolas L.,Macqueen, Preston M.,Lavoie, Christopher M.,McDonald, Robert,Stradiotto, Mark
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supporting information
p. 3773 - 3777
(2015/03/18)
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- Magnetically separable core-shell iron oxide@nickel nanoparticles as high-performance recyclable catalysts for chemoselective reduction of nitroaromatics
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A magnetically separable core-shell iron oxide@nickel (IO@Ni) nanocatalyst was synthesized by reduction of Ni2+ ions in the presence of iron oxide (Fe2+, Fe3+) by a simple one-pot synthetic route using NaBH4 as a reducing agent and starch as a capping agent. The synthesized nanoparticles (NPs) were characterized by several techniques such as X-ray diffraction (XRD), high resolution transmission electron microscopy (HR-TEM), selected area electron diffraction (SAED), and energy dispersive X-ray spectroscopy (EDS). The core-shell iron oxide@nickel nanoparticles (IO@NiNPs) were found to have excellent activity for the hydrogenation reactions of aromatic nitro compounds under mild conditions using water as a green solvent. Excellent chemoselectivity and recyclability up to 30 cycles for the nitro group reduction was demonstrated.
- Rathore, Puran Singh,Patidar, Rajesh,Shripathi,Thakore, Sonal
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p. 286 - 295
(2015/02/02)
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- In situ generation of ammonia for the copper-catalyzed synthesis of primary aminoquinolines
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The synthesis of primary aminoquinolines from iodoquinolines was carried out in the presence of copper(i) iodide and formamide as the solvent and source of ammonia generated in situ. The reaction proceeded under mild conditions within a few hours and was applicable to various iodoquinolines.
- Aillerie, Alexandre,Pellegrini, Sylvain,Bousquet, Till,Pélinski, Lydie
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p. 1389 - 1391
(2014/05/06)
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- Polymethylhydrosiloxane derived palladium nanoparticles for chemo- and regioselective hydrogenation of aliphatic and aromatic nitro compounds in water
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Chemo- and regioselective hydrogenation of a wide range of aliphatic, unsaturated, aromatic and heteroaromatic nitro compounds into their corresponding amines has been achieved with highly efficient polysiloxane-stabilised "Pd" nanoparticles on NAP-magnesium oxide supports using an environmentally friendly hydrogenating agent, polymethylhydrosiloxane [PMHS] in water. Highly stable and active Pd nanoparticles were prepared by the reduction of NAP-Mg-PdCl4 with PMHS, which serves as a reducing agent as well as a capping agent. The well-dispersed palladium nanoparticles on NAP-MgO catalysts also exhibit excellent regioselectivity in the hydrogenation of dinitrobenzenes to the corresponding nitroanilines. The catalyst has high durability against sintering during the hydrogenation reaction and can be reused with no loss in its activity. This journal is the Partner Organisations 2014.
- Damodara, Dandu,Arundhathi, Racha,Ramesh Babu, T. Venkata,Legan, Margaret K.,Kumpaty, Hephzibah J.,Likhar, Pravin R.
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p. 22567 - 22574
(2014/06/23)
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- Nickel nanoparticles as efficient catalyst for electron transfer reactions
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The catalytic efficiency of nickel nanoparticles was investigated in some electron transfer reactions. The nanoparticles brought about rapid roomtemperature reduction of a number of nitro aromatics in an aqueous medium with high chemoselectivity and also helped to speed up redox reaction of Fe(CN)-36and S2O-23. In addition, interesting results were obtained for microwave assisted decolourization of azo dye. The reactions were monitored through UV-Vis spectroscopy. The present study has additional advantages of reusability of catalysts and aqueous medium. The ultimate goal was to assess the suitability of low cost nanocatalyst for electron transfer reactions under aqueous conditions. Springer Science+Business Media New York 2013.
- Rathore, Puran Singh,Patidar, Rajesh,Rathore, Sonika,Thakore, Sonal
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p. 439 - 446
(2014/06/24)
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- Trifluoroacetic acid: An efficient catalyst for paal-knorr pyrrole synthesis and its deprotection
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In the present work, we demonstrated a simple and an efficient method for the condensation of substituted aryl/heteroaryl amines with acetonylacetone in the presence of trifluoro acetic acid to afford the corresponding 2,5-dimethyl-1-substitued pyrroles using Paal-Knorr synthesis in excellent yields. Trifluoroacetic acid was used under reflux condition for the deprotection of 2,5-dimethyl-1-substitued pyrroles to their corresponding substituted aryl/heteroaryl amines in moderate yields. 2,5-Dimethyl-1-substitued pyrrole were characterized by NMR and LC-MS. The yield of the compounds was found to be excellent.
- Venugopala, K. Narayanaswamy,Prasanna, Renuka T.,Odhav, Bharti
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p. 8685 - 8689
(2013/11/06)
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- Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts
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A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
- Cheung, Chi Wai,Surry, David S.,Buchwald, Stephen L.
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supporting information
p. 3734 - 3737
(2013/08/23)
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- Ethylacetoacetate tagged basic imidazolium salt: Multi-task in CuI nanoparticle catalyzed amination of aryl halides
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Copper catalyzed reactions suffer from harsh conditions of high temperature, high pressure, over-stoichiometric amount of copper reagents and use of expensive ligands. In an attempt to develop a mild, efficient and reusable system for copper catalyzed reactions, ethylacetoacetate was doped into ionic liquid (IL) by tagging it with imidazolium cation stabilized by a counter hydroxide or acetate anion (4a and 4b). The novel ligand-anchored ILs demonstrated high efficiency in generation and stabilization of uniformly dispersed Cu(I)I nanoparticles with particle size in range 9-12 nm. Further, the catalytic system provided an efficient route to amination of aryl iodides, bromides and the less reactive chlorides under mild conditions with very low catalyst loading of only 2 mol % to yield primary aryl amines selectively. Furthermore, the reaction allowed easy isolation of products with recovery of ionic liquid containing an intact built-in ligand and base combination for further reuse.
- Srivastava, Ananya,Jain, Nidhi
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p. 5092 - 5097
(2013/06/27)
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- Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia
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A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright
- Fantasia, Serena,Windisch, Johannes,Scalone, Michelangelo
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supporting information
p. 627 - 631
(2013/04/11)
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- One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds
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An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide.
- Maejima, Toshihide,Shimoda, Yutaka,Nozaki, Kei,Mori, Shigeki,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
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experimental part
p. 1712 - 1722
(2012/03/08)
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- An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide
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An efficient copper-catalyzedin in situ C-(sp2)-NH2 bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.
- Messaoudi, Samir,Brion, Jean-Daniel,Alami, Mouad
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experimental part
p. 1677 - 1687
(2010/10/01)
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- Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: A general method for the preparation of primary arylamines
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We report that the complex generated from Pd[P(o-tol)3] 2 and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates. The couplings of ammonia with this catalyst conducted with a solution of ammonia in dioxane form primary arylamines from a variety of aryl electrophiles in high yields. Catalyst loadings as low as 0.1 mol % were sufficient for reactions of many aryl chlorides and bromides. In the presence of this catalyst, aryl sulfonates also coupled with ammonia for the first time in high yields. A comparison of reactions in the presence of this catalyst versus those in the presence of existing copper and palladium systems revealed a complementary, if not broader, substrate scope. The utility of this method to generate amides, imides, and carbamates is illustrated by a one-pot synthesis of a small library of these carbonyl compounds from aryl bromides and chlorides, ammonia, and acid chlorides or anhydrides. Mechanistic studies show that reactions conducted with the combination of Pd[P(o-tol)3]2 and CyPF-t-Bu as catalyst occur with faster rates and higher yields than those conducted with CyPF-t-Bu and palladiun(II) as catalyst precursors because of the low concentration of active catalyst that is generated from the combination of palladium(II), ammonia, and base.
- Vo, Giang D.,Hartwig, John F.
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supporting information; experimental part
p. 11049 - 11061
(2009/12/05)
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- Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst
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A variety of aryl and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst. The Royal Society of Chemistry.
- Ntaganda, Rukundo,Dhudshia, Bhartesh,Macdonald, Charles L. B.,Thadani, Avinash N.
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supporting information; experimental part
p. 6200 - 6202
(2009/05/06)
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- Fluorous-tagged carbamates for the Pd-catalyzed amination of aryl halides
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(Chemical Equation Presented) A novel fluorous-tagged ammonia surrogate has been synthesized and its application to the synthesis of anilines by Buchwald-Hartwig palladium-catalyzed amidation-hydrolysis protocol is described. Primary anilines were obtained in moderate to good yields after a sequence of two reaction steps involving fluorous separation techniques for their purification. Preliminary results indicate that N-substituted anilines can also be obtained using just N-substituted-FBoc carbamates as the nitrogen source.
- Trabanco, Andres A.,Vega, Juan A.,Fernandez, M. Alejandro
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p. 8146 - 8148
(2008/02/12)
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- Amination of aryl halides using copper catalysis
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Bromopyridine 4 was converted into aminopyridine 5 under Cu2O catalysis with an ethylene glycol solution of ammonia in excellent yield (90%). The amination reaction features low (0.5 mol%) catalyst loading, mild reaction temperature (80°C) and low reaction pressure (50 psi). This protocol is further studied in the amination of a variety of aryl halides.
- Lang, Fengrui,Zewge, Daniel,Houpis, Ioannis N.,Volante
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p. 3251 - 3254
(2007/10/03)
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- Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines
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A series of anilines and heteroarylamines were synthesized in moderate to excellent yields by palladium catalyzed cross coupling reaction of aryl or heteroaryl halides with allyl- or N,N-diallylamine followed by deallylation.
- Jaime-Figueroa, Saul,Liu, Yanzhou,Muchowski, Joseph M.,Putman, David G.
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p. 1313 - 1316
(2007/10/03)
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- PHOTOLYSIS AND THERMOLYSIS OF QUINOLYL AND ISOQUINOLYL AZIDES IN ETHANETHIOL
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3-Quinolyl azides (8), upon either irradiation or heating in ethanethiol, gave 3-amino-4-ethylthioquinolines (9), presumably via a radical process.Similarly, 4-isoquinolyl azides (11) gave 3-ethyl-thio- (12) and/or 1-ethylthio-4-aminoisoquinolines (13), and 8-quinolyl azide (17) gave 7-ethylthio- (18) and 5-ethylthio-8-aminoquinoline (19), while 4-quinolyl azides (15) gave only 8-aminoquinolines (16).
- Sawanishi, Hiroyuki,Hirai, Toyoko,Tsuchiya, Takashi
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p. 1501 - 1504
(2007/10/02)
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- Photolysis of Quinolyl and Isoquinolyl Azides in the Presence of Methoxide Ions. Synthesis of Benzodiazepines and Pyridoazepines
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Photolysis of the title compounds in the presence of methoxide provides a convenient preparation of the corresponding methoxy-substituted bicyclic azepines and benzodiazepines in one step from readily available starting materials.Moreover, the methoxy-group in the azepines is replaceable by amines.
- Hollywood, Frank,Khan, Zafar U.,Scriven, Eric F. V.,Smalley, Robert K.,Suschitzky, Hans,et al.
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p. 431 - 433
(2007/10/02)
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- Photolysis of Quinolyl and Isoquinolyl Azides in Primary and Secondary Aliphatic Amines: Synthesis of Bicyclic Azepines, Diazepines, and Quinolyl- and Isoquinolyl-diamines
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Photolysis of the title compounds in primary aliphatic amines gave in some cases bicyclic azepines and diazepines as well as o-diamines, while in secondary amines mainly the appropriate o-diamines are obtained.On the basis of the many examples studied guidelines are put forward to predict the nature of products from photolysis of bicyclic azides in primary and secondary amines and to obtain maximum yields.
- Hollywood, Frank,Nay, Barry,Scriven, Eric F. V.,Suschitzky, Hans,Khan, Zafar U.,Hull, Roy
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p. 421 - 429
(2007/10/02)
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- Synthesis and Chemical Properties of 3-Aminoquinoline
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Reaction of 3-bromoquinoline with ammonia gives 3-aminoquinoline (3) in good yield.Substitution of 3 is possible by treating the sodium salt of 3 with alkyl halides or by reductive alkylation with aromatic and aliphatic ketones.Amine exchange occurs by reaction of acetophenone Mannich bases with 3.Methyl vinyl ketone and acrylonitrile give no addition compounds with 3.Derivatives of trans-3-phenylglycidic acid react with 3 to give derivatives of β-phenylisoserine.
- Schoenen, Beate,Zymalkowski, Felix
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p. 464 - 470
(2007/10/02)
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- Thermal Decomposition of Aromatic Azides. Formation of Phenazines and Related Compounds
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The decomposition of some aromatic azides yielding significant amounts of phenazines, and thereby constituting a potential synthetic procedure, is reported.
- Nay, Barry,Scriven, Eric F. V.,Suschitzky, Hans,Thomas, Desmond R.
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p. 611 - 613
(2007/10/02)
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