- GAS-PHASE BASICITY AND IONIZATION ENERGIES IN SOME N-ARYLAZACYCLOALKANES
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Proton-transfer equilibrium constant and ionization energy measurement were performed in the gas phase for a series of N-arylazacycloalkanes.The techniques used were Fourier transform ion cyclotron resonance (FT-ICR) and UV photoelectron spectroscopy (UPS
- Cauletti, C.,Cerichelli, G.,Grandinetti, F.,Luchetti, L.,Speranza, M.
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Read Online
- Direct Near Infrared Light–Activatable Phthalocyanine Catalysts
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The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa
- Katsurayama, Yoshino,Ikabata, Yasuhiro,Maeda, Hajime,Segi, Masahito,Nakai, Hiromi,Furuyama, Taniyuki
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supporting information
(2021/12/22)
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- Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis
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Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)-H bonds was demonstrated by a series of experimental and computational studies.
- Xiao, Teng-Fei,Zhang, Yi-Fan,Hou, Wen-Tao,Yan, Pen-Ji,Hai, Jun,Xu, Peng-Fei,Xu, Guo-Qiang
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supporting information
p. 8942 - 8946
(2021/11/24)
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- Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles
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A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.
- Yi, Ming-Jun,Xiao, Teng-Fei,Li, Wen-Hui,Zhang, Yi-Fan,Yan, Pen-Ji,Zhang, Baoxin,Xu, Peng-Fei,Xu, Guo-Qiang
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supporting information
p. 13158 - 13161
(2021/12/16)
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- I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of: N -aryl-substituted azacycles
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We have developed a protocol for efficient synthesis of N-aryl-substituted azacycles from aryl amines and cyclic ethers using I2/NaH2PO2 as the mediator. A diverse range of aryl amines and cyclic ethers undergo amination reaction to generate products in good to excellent yields with good functional group tolerance. This reaction can be easily scaled up to give N-aryl-substituted azacycles on a gram scale. Further chemical manipulation of the products enabled useful transformations of the quinoline ring, including bromination and acetylation. This journal is
- Chen, Tieqiao,Huang, Tianzeng,Li, Chunya,Li, Dongyang,Lin, Ying,Liu, Long,Tang, Zhi,Zhang, Jingjing
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supporting information
p. 21011 - 21014
(2021/12/04)
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- Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU
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A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.
- Kang, Soosung,Kim, Hee-Kwon,La, Minh Thanh,Tran, Van Hieu
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p. 5008 - 5016
(2020/07/30)
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- Organocatalytic Cascade β-Functionalization/Aromatization of Pyrrolidines via Double Hydride Transfer
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An unprecedented cascade β-functionalization/aromatization reaction of N-arylpyrrolidines was established. A series of β-substituted arylpyrroles embedded with trifluoromethyl groups are provided directly from N-arylpyrrolidines. The deuterium-labeling experiments indicate that sequential double hydride transfer processes serve as the key steps in this transformation.
- An, Xiao-De,Li, Xian-Jiang,Liu, Qing,Shao, Chang-Lun,Xiao, Jian,Yang, Shuo,Zhou, Lan
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supporting information
(2020/02/15)
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- N-heterocyclic carbene-Pd(II)-2-methyl-4,5-dihydrooxazole complex-catalyzed highly chemoselective mono-amination of dichlorobenzenes
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The palladium-catalyzed chemoselective mono-amination of dichlorobenzenes was reported in this paper. Under the suitable conditions, all reactions involving the three isomers of dichlorobenzenes with various secondary and primary amines in the presence of
- He, Qian-Wei,Lu, Jian-Mei,Shao, Li-Xiong,Sun, Kai-Xin,Zhou, Jin-Hui
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- Tropane alkaloid compounds and method of manufacturing using sequential oxidation reactions
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The present invention relates to a tropane alkaloid compound sequentially using an oxidative Mannich ring reaction and a method for producing the same. The present invention provides a tropane alkaloid compound having a structure of chemical formula 1 in
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Paragraph 0098; 0153-0157
(2020/06/16)
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- Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy
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Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.
- Yao, Wei,Ge, Chenyang,Zhang, Yilin,Xia, Xiao-Feng,Wang, Long,Wang, Dawei
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supporting information
p. 16099 - 16105
(2019/11/26)
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- Redox-Neutral β-C(sp3)-H Functionalization of Cyclic Amines via Intermolecular Hydride Transfer
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Herein, we report the first redox-neutral and transition-metal-free β-C(sp3)-H functionalization of cyclic amines via a consecutive intermolecular hydride transfer process. A series of N-aryl pyrrolidines and N-aryl 1,2,3,4-tetrahydropyridines decorated with CF3 and carboxylic ester functionalities are directly accessed in good yields from pyrrolidines and piperidines. This work pushes forward the application of the intermolecular hydride transfer strategy in one-step assembly of molecular complexity.
- Zhou, Lan,Shen, Yao-Bin,An, Xiao-De,Li, Xian-Jiang,Li, Shuai-Shuai,Liu, Qing,Xiao, Jian
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supporting information
p. 8543 - 8547
(2019/11/03)
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- Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide
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We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.
- Tan, Wei,Wang, Cuihong,Jiang, Xuefeng
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supporting information
p. 1234 - 1238
(2019/11/21)
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- Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions
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Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.
- Xu, Guo-Qiang,Xu, Ji-Tao,Feng, Zhi-Tao,Liang, Hui,Wang, Zhu-Yin,Qin, Yong,Xu, Peng-Fei
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supporting information
p. 5110 - 5114
(2018/03/27)
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- Transition-Metal-Free Selective C?H Benzylation of Tertiary Arylamines by a Dearomatization-Aromatization Sequence
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Due to the significance of hybrid systems in drug discovery, there is an urgent need to assemble multiple biologically active ingredients into a single molecule. Here, we report a general transition-metal-free selective C?H benzylation of tertiary arylamines in good to excellent yields with a broad substrate scope and high functional-group tolerance under mild conditions. Besides arylamines, some other benzene derivatives also readily furnished the corresponding diaryl methane derivatives with this protocol. A series of control experiments and theoretical calculations indicated that this transition-metal-free reaction is a dearomatization-aromatization process.
- Xu, Guo-Qiang,Feng, Zhi-Tao,Xu, Ji-Tao,Wang, Zhu-Yin,Qin, Yong,Xu, Peng-Fei
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supporting information
p. 13778 - 13782
(2018/09/14)
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- New N-substituted tetrahydropyrrole derivative synthesis method
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The invention provides an amino boron intermediate-mediated synthesis method for preparing N-substituted tetrahydropyrrole derivatives by using aromatic amine and a five-membered oxygen heterocyclic compound as raw materials. According to the present invention, the N-substituted tetrahydropyrrole derivatives are specifically N-aryltetrahydropyrrole and N-aryl 2-methyltetrahydropyrrole, and have the following chemical structure general formulas, wherein Ar is phenyl, 4-methylphenyl, 4-fluorophenyl, 4-chlorophenyl, 2-chlorophenyl, 3-nitrophenyl, 2,4-difluorophenyl, 2,6-dichlorophenyl or 3,5-dichlorophenyl. The present invention discloses the chemical structures and the synthesis method of the compounds.
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Paragraph 0018-0019
(2019/11/13)
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- Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines
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A concise synthesis of 8-azabicyclo[3.2.1]octanes via sequential oxidative Mannich reactions is described. This approach involves an intermolecular oxidative Mannich coupling reaction between N-aryl pyrrolidines with TMS enol ether and a subsequent intramolecular oxidative Mannich cyclization of the corresponding silyl enol ether. DDQ is used as a key oxidant for both reactions.
- Jo, Hanbyeol,Hassan, Ahmed H. E.,Jung, Seung Young,Lee, Jae Kyun,Cho, Yong Seo,Min, Sun-Joon
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supporting information
p. 1175 - 1178
(2018/02/23)
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- Synthetic method for five-component and six-component N-substituted nitrogenous heterocyclic compounds
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The invention provides a synthetic method for preparing five-component and six-component N-substituted nitrogenous heterocyclic compounds from aromatic amine and five-component and six-component oxygen heterocyclic compounds via mediation by an aminotitanium intermediate. The five-component and six-component N-substituted nitrogenous heterocyclic compounds provided by the invention specifically refer to N-aryltetrahydropyrrole, N-aryl-2-methyltetrahydropyrrole, N-aryltetrahydropyrane, N-aryl-3,4-dihydro-1H-2-pyrane with a general chemical formula as defined in the specification. In the formula, Ar is a phenyl group, a 4-methylphenyl group, a 2-halophenyl group, a 3-halophenyl group or a 4-halophenyl group. The invention discloses the chemical structures and synthetic method of the compounds.
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Paragraph 0018; 0019
(2017/02/09)
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- Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers
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Titanium tetrachloride-mediated transformation of five- and six-membered cyclic ethers to the corresponding N-aryl-substituted azacycles is conducted in moderate to good yields under mild reaction conditions. Computational studies suggested a mechanism involving a Lewis acid-assisted ring-opening, a seven-membered metallacycle intermediate and a ring-closing process facilitated by direct participation of the metal center.
- Sun, Zunming,Hu, Shanshan,Huo, Yan,Wang, Zhihong
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p. 4363 - 4367
(2017/01/29)
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- Boron trifluoride-mediated synthesis of N-aryl-substituted pyrrolidines from tetrahydrofuran and amines
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[Figure not available: see fulltext.] Boron trifluoride-mediated transformation of tetrahydrofuran to corresponding N-aryl-substituted pyrrolidines is conducted under mild reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing process as the rate-determining step.
- Hu, Shanshan,Huo, Yan,Wang, Zhihong
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p. 1365 - 1368
(2018/01/27)
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- Copper-catalyzed C-N bond cross-coupling of aryl halides and amines in water in the presence of ligand derived from oxalyl dihydrazide: Scope and limitation
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An efficient and convenient method has been developed for the copper-catalyzed C-N bond cross-coupling of aryl bromides with electron-donor substituents and aliphatic amines in water. The new ligand system N-phenyloxalyl bishydrazide/hexane-2,5-dione has been shown to be considerably more efficient in the copper-catalyzed C-N bond cross-coupling reaction as compared to the ligands described in the literature and allowed decreasing of the catalyst amount (up to 2 mol %) to achieve acceptable yields of isolated products (46-84%). Acceptor substituted aryl bromides, aryl bromides with substituents in the ortho-position, and some aryl dichlorides can undergo the C-N cross-coupling under the developed conditions, but their reactivity is lower.
- Kurandina,Eliseenkov,Khaibulova,Petrov,Boyarskiy
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p. 7931 - 7937
(2015/09/15)
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- Synthesis of N-arylsubstituted pyrrolidines and piperidines by reaction of anilines with α,ω-diols catalyzed by FeCl3·6H2O in carbon tetrachloride
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N-Arylpyrrolidines and N-arylpiperidines were synthesized in 20-88% yields by the reaction of aniline and aniline derivatives with 1,4-butane- and 1,5-pentanediols in the presence of Fecontaining catalysts and carbon tetrachloride. 1,4-Butane- and 1,5-pentanediols are partially chlorinated under the reaction conditions to give chlorohydrins, which subsequently undergo Nheterocyclization with anilines to give N-arylpyrrolidines and N-arylpiperidines.
- Khusnutdinov, Ravil I.,Bayguzina, Alfiya R.,Asylbaeva, Rigina S.,Aminov, Rishat I.,Dzhemilev, Usein M.
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p. 341 - 350
(2014/12/12)
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- Iron(III)-catalyzed C-H functionalization: Ortho-benzoyloxylation of N,N-dialkylanilines and its application to 1,4-benzoxazepines
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A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyl-oxylation of a variety of N,N-disubstituted anilines and Nphenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and oaminophenols.
- Chiranjeevi, Barreddi,Vinayak, Botla,Parsharamulu, Thupakula,PhaniBabu, Vemulapalli S.,Jagadeesh, Bharatam,Sridhar, Balasubramanian,Chandrasekharam, Malapaka
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p. 7839 - 7849
(2015/01/16)
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- Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes
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Synthesis of N-aryl substituted, five- and six-membered azacycloalkanes, isoindolines and tetrahydroisoquinolines, has been described. In this synthesis, cyclic ethers (n = 1, 2) were treated with dimethylaluminum-amide reagents, derived from a range of aryl amines and trimethylaluminum, to afford the corresponding azacycles in good yields. This journal is the Partner Organisations 2014.
- Korbad, Balaji L.,Lee, Sang-Hyeup
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supporting information
p. 8985 - 8988
(2014/08/05)
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- Microwave-assisted convenient synthesis of N-arylpyrrolidines in water
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An efficient and clean synthesis of N-arylpyrrolidines from arylamines and 1,4-dimesyloxybutane was developed using microwave irradiation in an aqueous potassium carbonate medium without any catalyst. The procedure is rapid, simple and convenient.
- Li, Hong Bo,Liang, Wu,Liu, Lang,Chen, Kai,Wu, Yi
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experimental part
p. 276 - 279
(2012/01/05)
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- Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines
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The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.
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Page/Page column 7
(2012/01/13)
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- C-N bond formation catalysed by CuI Bonded to polyaniline nanofiber
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Polyaniline nanofiber as a macroligand for the supported cuprous iodide catalyst (CuI-PANInf) has been developed for the coupling of aryl halides (including aryl chlorides) with aliphatic, aromatic, and N(H)-heterocyclic amines under ambient conditions (80 °C for aryl chlorides) has been developed. This simple and efficient method for coupling reactions is highly versatile, convenient, and also the catalyst can be used for several cycles with good-to-excellent yields.
- Arundhathi, Racha,Kumar, Desitti Chaitanya,Sreedhar, Bojja
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supporting information; experimental part
p. 3621 - 3630
(2010/08/20)
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- Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology
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The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.
- Hamid, M. Haniti S. A.,Allen, C. Liana,Lamb, Gareth W.,Maxwell, Aoife C.,Maytum, Hannah C.,et al.
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supporting information; experimental part
p. 1766 - 1774
(2009/07/25)
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- A novel salt-free ruthenium-catalyzed alkylation of aryl amines
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The alkylation of aryl amines using cyclic amines such as pyrrolidine proceeds via borrowing hydrogen methodology in the presence of 1 mol % Shvo catalyst. During the reaction multiple carbon-nitrogen cleavage and formation occurred. This novel reaction sequence leads to N-aryl-pyrrolidines and -piperidines.
- Hollmann, Dirk,B?hn, Sebastian,Tillack, Annegret,Parton, Rudy,Altink, Rinke,Beller, Matthias
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p. 5742 - 5745
(2008/12/22)
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- CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature
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We have developed an efficient and readily available catalyst system CuBr/racemic BINOL ( 1,1′-binaphthyl-2,2′-diol) that catalyzes N-arylation of aliphatic amines at room temperature, and this inexpensive catalyst system is of high selectivity and tolerance toward various functional groups in the substrates.
- Jiang, Deshou,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 672 - 674
(2007/10/03)
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- A mild and efficient method for copper-catalyzed Ullmann-type N-arylation of aliphatic amines and amino acids
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An efficient and general protocol for copper-catalyzed N-arylation of aliphatic amines and amino acids has been developed using aryl iodides under mild conditions (coupling temperature at 25-35°C). For the N-(o-nitrophenyl) amino acid derivatives, subsequent reduction of the nitro group in the presence of tin(II) chloride resulted in 3,4-dihydroquinoxalin-2(1H)-one derivatives in good yields. Georg Thieme Verlag Stuttgart New York.
- Jiang, Qun,Jiang, Deshou,Jiang, Yuyang,Fu, Hua,Zhao, Yufen
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p. 1836 - 1842
(2008/02/10)
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- Anodic cyanation of 1-arylpyrrolidines
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The electrochemical cyanation of 1-arylpyrrolidines was carried out in methanol containing sodium cyanide at a platinum anode in a divided cell. The reaction gave the corresponding α-aminonitriles 2, together with the unexpected 1-arylpyrrolidine-2-carboximidic acid methyl esters 3 as byproducts.
- Liu, Wei,Ma, Yuan,Yin, Yingwu,Zhao, Yufen
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p. 577 - 579
(2007/10/03)
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- Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles
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CuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliphatic primary amines occurs at 40 °C under the promotion of N-methylglycine. Using L-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliphatic primary amines, aliphatic cyclic secondary amines, or electron-rich primary arylamines proceeds at 60-90 °C; an intramolecular coupling reaction between aryl chloride and primary amine moieties gives indoline at 70 °C; coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole can be carried out at 75-90 °C; and coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 °C to provide the corresponding N-aryl products in good to excellent yields. In addition, N,N-dimethylglycine promotes the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles or pyrazoles at 110 °C. The possible action of amino acids in these coupling reactions is discussed.
- Zhang, Hui,Cai, Qian,Ma, Dawei
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p. 5164 - 5173
(2007/10/03)
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- Microwave-assisted amination from aryl triflates without base and catalyst
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(Equation presented) Aryl triflates are effectively converted to the corresponding anilines under microwave irradiation in 1-methyl-2-pyridone (NMP) without base and catalyst. Aryl triflates substituted with both electron-poor and electron-rich groups give good to excellent yields. It is noteworthy that the halogenated aryl triflates can chemoselectively react with amines to afford halogenated anilines.
- Xu, Gang,Wang, Yan-Guang
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p. 985 - 987
(2007/10/03)
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- A simple route to N-ω-chloroalkylisatins from cyclic t-anilines, oxalyl chloride and DABCO
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para-Substituted N-phenylpyrrolidines, -piperidines, -perhydroazepines and -morpholines react with oxalyl chloride and DABCO to give the pharmaceutically useful intermediates, N-ω-haloalkylisatins, under mild conditions and generally good yields.
- Cheng,Zhan,Meth-Cohn
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- Substituent effects in the gas-phase pyrolysis of 4-(N/-arylamino)-1-butyl acetate and 5-(N/-arylamino)-1-pentyl acetate
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A kinetic study of the gas-phase pyrolysis of 4- and 5-(N-arylamino)-1-butyl and -1-pentyl acetate was mace. Each ester was pyrolysed at five or six different temperatures and over a temperature range not less than 50 °C. These reactions were homogeneous and unimolecular. The reactivities of these compounds were compared with those of the parent compounds 4- and 5-(N-phenyl)-1-butyl and -1-pentyl acetate and with each other. The products of the decomposition reaction of these compounds suggest an anchimeric assistance of the amino substituen for a trans elimination, indicating that an ion-pair type of mechanism may be operating during the process of elimination. Copyright
- Al-Awadi, Nouria A.,Elnagdi, Mohamed H.,Kaul, Kamini,Chuchani, Gabriel
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p. 675 - 678
(2007/10/03)
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- Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran
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The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.
- Verardo, Giancarlo,Dolce, Anna,Toniutti, Nicoletta
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- Ruthenium Complex-Catalyzed N-Heterocyclization. Syntheses of N-Substituted Pyrroles and Pyrrolidines from 1,4-Diols and Primary Amines
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2-Butyne-1,4-diol reacts with aliphatic amines in the presence of a catalytic amount of at 150 deg C to give N-alkylpyrroles in good yields. 1,4-Butanediol reacts with aromatic or aliphatic amines to give N-substituted pyrrolidines in excellent yields; and are the best catalysts for aromatic and aliphatic amines, respectively.The reaction of 2-butene-1,4-diol with alkyl amines gives a 1:1 mixture of N-substituted pyrroles and pyrrolidines in high yield.
- Tsuji, Yasushi,Yokoyama, Yasuharu,Huh, Keun-Tae,Watanabe, Yoshihisa
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p. 3456 - 3458
(2007/10/02)
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- A NEW AND FACILE SYNTHESIS OF N-SUBSTITUTED PYRROLIDINE OF AMINES WITH AQUEOUS SUCCINALDEHYDE USING TETRACARBONYLHYDRIDOFERRATE, HFe(CO)4(1-), AS A HIGHLY SELECTIVE REDUCING AGENT.
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Ethanolic tetracarbonylhydridoferrate combined with aqueous succinaldehyde is very efficient for the selective transformation of an amino group into a pyrrolidine ring.A large variety of both aliphatic and aromatic amines react with aqueous succinaldehyde in the presence of tetracarbonylhydridoferrate at room temperature under carbon monoxide to give the corresponding N-alkyl- and N-arylpyrrolidines in good to excellent yields.
- Shim, Sang Chul,Huh, Keun Tai,Park, Woo Hiun
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p. 259 - 264
(2007/10/02)
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- Stereoelectronic Effects in Tertiary Amine Nitrosation: Nitrosative Cleavage vs. Aryl Ring Nitration
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The nitrosation (acetic acid) of N-(4-chlorophenyl)pyrrolidine gives at least 30percent N-(4-chloro-2-nitrophenyl)pyrrolidine while the corresponding aryldibenzylamine gives no nitration and only nitrosative dealkylation at nitrogen.This difference in reaction site has been probed with N-(4-chlorophenyl)diethylamine.This substance undergoes competitive ring nitration to N-(4-chloro-2-nitrophenyl)diethylamine (50percent) and nitrosative dealkylation to (4-chlorophenyl)ethylnitrosamine (50percent).The former compound nitrosates further to give (4-chloro-2-nitrophenyl)ethylnitrosamine.This substance denitrosates to give the corresponding secondary amine.The reactivity differences result from stereoelectronic factors controlling the amine nitrogen unshared pair delocalization into the aryl ring.This interpretation is supported by 13C NMR data and mechanistic arguments.
- Leoppky, Richard N.,Tomasik, Witold
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p. 2751 - 2757
(2007/10/02)
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