- Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles
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An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.
- Delgado, Francisco,Gutiérrez, Rsuini U.,Hernández-Montes, Mayra,Mendieta-Moctezuma, Aarón,Tamariz, Joaquín
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- Aniline-initiated and Br?nsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR
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A highly novel method of direct synthesis of 2-aryl-3-sulfenylindoles in moderate to good yields was developed via one-pot tandem reaction of readily available α-aminocarbonyl compounds and catalytic amount of benzenamines with RSSR.
- Chen, De,Cheng, Chaozhihui,Deng, Wei,Guan, Wenjian,Liu, Yuxuan,Luo, Yongyue,Xiang, Jiannan,Zhang, Jiajia
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- Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
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Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
- Chen, Shaomin,Gu, Yanlong,Li, Minghao
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supporting information
p. 10431 - 10434
(2021/10/12)
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- An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
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We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
- Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
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supporting information
p. 9610 - 9616
(2021/12/09)
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- B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
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An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.
- Yuan, Wenkai,Huang, Jie,Xu, Xin,Wang, Long,Tang, Xiang-Ying
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supporting information
p. 7139 - 7143
(2021/09/14)
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- Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
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Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
- Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
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supporting information
p. 10242 - 10245
(2021/10/12)
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- Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization
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Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.
- Choudhury, Joyanta,Dutta, Tapas Kumar,Mandal, Tanmoy,Mohanty, Sunit
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supporting information
p. 10182 - 10185
(2021/10/12)
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- Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones
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A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.
- Dong, Chun-Lin,Ding, Xuan,Huang, Lan-Qian,He, Yan-Hong,Guan, Zhi
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supporting information
p. 1076 - 1080
(2020/02/15)
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- Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
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A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
- Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
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supporting information
p. 3294 - 3299
(2020/01/21)
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- Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
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The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.
- Black, Gary W.,Brancale, Andrea,Castagnolo, Daniele,Colonna, Serena,Ferla, Salvatore,Masci, Domiziana,Turner, Nicholas J.,Varricchio, Carmine,Zhao, Fei
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p. 6414 - 6421
(2020/07/09)
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- α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
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Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
- Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
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p. 7433 - 7445
(2020/06/27)
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- Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source
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A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.
- Guan, Xinyu,Zhu, Haoran,Zhao, Yingwei,Driver, Tom G.
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supporting information
p. 57 - 60
(2019/12/11)
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- Well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes-catalyzed direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides
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A series of well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes (N–heterocyclic carboxylate = pyridine-2-carboxylate, quinoline-2-carboxylate and isoquinoline-1-carboxylate) were synthesized and fully characterized by NMR spectra, HR-MS and X-ray single crystal diffraction. The obtained complexes were then used for direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides. With low catalyst loading, all complexes exhibited high catalytic activities for the arylation reactions.
- Yang, Jin,Zong, Ling-Li,Zhu, Xiao-Ting,Zhu, Xin-Ying,Zhao, Jian-Yi
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- Characterization of heterogeneous aryl-Pd(ii)-oxo clusters as active species for C-H arylation
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C-H arylation with heterogeneous palladium was investigated. The surface oxidation of Pd nanoparticles with a hypervalent iodine reagent, [Ph2I]BF4, resulted in the generation of Pd(ii)-aryl-oxo clusters, which were characterized as the crucial intermediate.
- Shin, Taeil,Kim, Minjun,Jung, Younjae,Cho, Sung June,Kim, Hyunwoo,Song, Hyunjoon
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supporting information
p. 14404 - 14407
(2020/12/01)
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- Synthetic method of 2-substituted indoles compounds
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The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.
- -
-
Paragraph 0010; 0035-0037; 0039-0040; 0146-0147
(2019/05/02)
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- A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water
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The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.
- Vaidya, Gargi Nikhil,Fiske, Sneha,Verma, Hansa,Lokhande, Shyam Kumar,Kumar, Dinesh
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supporting information
p. 1448 - 1454
(2019/03/26)
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- Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers
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The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described.
- Umareddy, Pailla,Arava, Veera Reddy
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supporting information
p. 2156 - 2167
(2019/07/04)
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- Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles
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Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition-metal-free assembly of 2-aryl indoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.
- Mao, Jianyou,Wang, Zhiting,Xu, Xinyu,Liu, Guoqing,Jiang, Runsheng,Guan, Haixing,Zheng, Zhipeng,Walsh, Patrick J.
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supporting information
p. 11033 - 11038
(2019/07/08)
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- Method for directly synthesizing indole by using nitrile
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The invention discloses a method for directly synthesizing indole by using nitrile. The method is characterized in that a 2-iodotoluene derivative is served as a substrate, anhydrous copper sulfate, potassium tert-butoxide, a cyanophenyl derivative and the 2-iodophene derivative are mixed according to the molar ratio of (0.02-0.1): (2-4): (5-20):1, reaction is carried out for 4-48 hours at 60-105DEG C in a solvent, petroleum ether/dichloromethane/ethyl acetate are mixed according to the volume ratio of (20-5):10:1 so as to be served as an eluent, and separation is carried out by using a silica gel column so as to obtain a target product. The method has the advantages that the operation is simple, the conditions are mild, the yield is high, and the method is a green and novel synthetic method.
- -
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Paragraph 0027-0029
(2018/12/13)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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supporting information
p. 3527 - 3530
(2018/06/26)
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- Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant
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Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.
- Shevlin, Michael,Guan, Xinyu,Driver, Tom G.
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p. 5518 - 5522
(2017/08/17)
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- Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation
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A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.
- Gao, Yadong,Zhu, Wangying,Yin, Long,Dong, Bo,Fu, Jingjing,Ye, Zhiwen,Xue, Fengtian,Jiang, Chao
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supporting information
p. 2213 - 2216
(2017/05/16)
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- Pd-PEPPSI-IPentCl: A new highly efficient ligand-free and recyclable catalyst system for the synthesis of 2-substituted indoles: Via domino copper-free Sonogashira coupling/cyclization
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A pyridine-containing decidedly resourceful Pd-N-heterocyclic carbene complex, Pd-PEPPSI-IPentCl (PEPPSI = pyridine enhanced precatalyst preparation, stabilization, and initiation), is used as a first class recyclable catalytic system for the synthesis of 2-substituted indoles via domino copper-free Sonogashira coupling/cyclization. The catalyst showed a greater performance in the cascade reaction of various 2-bromo anilines with different terminal acetylenes under mild (60 °C) and green conditions (ethanol:water) even in the absence of a copper catalyst and an inert atmosphere. The catalyst is used for the first time in these reactions. The findings suggest that 0.1 mol% of the catalyst is sufficient, and that the catalyst is recyclable and can be reused for up to six cycles.
- Kolli, Murali Krishna,Shaik, Nagul Meera,Chandrasekar, Govindasamy,Chidara, Sridhar,Korupolu, Raghu Babu
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p. 8187 - 8195
(2017/08/15)
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- Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
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Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
- Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
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supporting information
p. 4277 - 4281
(2017/04/03)
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- Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles
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An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
- Liu, Congrong,Yang, Fulai
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supporting information
p. 1213 - 1217
(2016/12/28)
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- Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides
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A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.
- Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei,Yang, Fu-Lai
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p. 2824 - 2827
(2016/03/12)
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- Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform
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The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.
- Huang, Yuan-Biao,Shen, Min,Wang, Xusheng,Huang, Ping,Chen, Ruiping,Lin, Zu-Jin,Cao, Rong
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- Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
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3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.
- Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Matheny, Jonathon P.,Rubin, Michael
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p. 8647 - 8656
(2015/03/03)
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- Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide
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The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.
- Zhou, Fei,Wang, Duo-Sheng,Driver, Tom G.
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p. 3463 - 3468
(2016/01/25)
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- Cobalt catalyzed sp3 C-H amination utilizing aryl azides
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A dinuclear Co(ii) complex supported by a modular, tunable redox-active ligand system is capable of selective C-H amination to form indolines from aryl azides in good yields at low (1 mol%) catalyst loading. The reaction is tolerant of medicinally relevant heterocycles, such as pyridine and indole, and can be used to form 5-, 6-, and 7-membered rings. The synthetic versatility obtained using low loadings of an earth abundant transition metal complex represents a significant advance in catalytic C-H amination technology.
- Villanueva, Omar,Weldy, Nina MacE,Blakey, Simon B.,MacBeth, Cora E.
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p. 6672 - 6675
(2015/10/28)
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- A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions
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Privileged structures such as 2-arylindoles are recurrent molecular scaffolds in bioactive molecules. We here present an operationally simple, high yielding and scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions
- Johansson, Henrik,Urruticoechea, Andoni,Larsen, Inna,Sejer Pedersen, Daniel
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p. 471 - 481
(2015/08/25)
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- Enantioselective arylative dearomatization of indoles via pd-catalyzed intramolecular reductive heck reactions
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A highly enantioselective intramolecular arylative dearomatization of indoles via palladium-catalyzed reductive Heck reactions was developed. The new strategy led to a series of optically active indolines bearing C2-quaternary stereocenters in modest to good yields with excellent enantioselectivities (up to 99% ee).
- Shen, Chong,Liu, Ren-Rong,Fan, Ren-Jie,Li, Ying-Long,Xu, Teng-Fei,Gao, Jian-Rong,Jia, Yi-Xia
-
supporting information
p. 4936 - 4939
(2015/05/05)
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- Multi-site cyclization via initial C-H activation using a rhodium(III) catalyst: Rapid assembly of frameworks containing indoles and indolines
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Tandem multi-site cyclization triggered by Rh(III)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.
- Huang, Ji-Rong,Qin, Liu,Zhu, Yu-Qin,Song, Qiang,Dong, Lin
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supporting information
p. 2844 - 2847
(2015/03/05)
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- Benzofuran derivatives as anticancer inhibitors of mTOR signaling
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A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed with rapamycin derivatives currently used in clinic.
- Salomé, Christophe,Ribeiro, Nigel,Chavagnan, Thierry,Thuaud, Frédéric,Serova, Maria,De Gramont, Armand,Faivre, Sandrine,Raymond, Eric,Désaubry, Laurent
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supporting information
p. 181 - 191
(2014/06/09)
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- Anticonvulsant evaluation of clubbed indole-1,2,4-triazine derivatives: A synthetic approach
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A series of thirty indole C-3 substituted 5-amino-6-(5-substituted-2- phenyl-1H-indol-1-yl)-4,5-dihydro-1,2,4-triazine-3(2H)-thione 5a-f, 6a-f, 7a-f, 8a-f and 9a-f were synthesized to explore prospective anticonvulsant agents. The derivative 1-(1-(5-amino
- Ahuja, Priya,Siddiqui, Nadeem
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p. 509 - 522
(2014/05/20)
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- Pd(II)/Bu4NBr/DMSO catalytic system for practical synthesis of indoles and pyrroles from imines through aerobic dehydrogenative cyclization
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N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole deriva
- Tan, Wei Wen,Hou, Xiaoya,Yoshikai, Naohiko
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p. 2727 - 2733
(2015/05/05)
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- Mild Rh(III)-catalyzed direct C-H bond arylation of (hetero)arenes with arylsilanes in aqueous media
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An efficient rhodium(III)-catalyzed C-H bond activation and further direct arylation of (hetero)arenes with organosilanes in aqueous media was developed. This reaction shows good substrate scope and excellent functional group compatibility and gives the products in good yields with excellent regioselectivity.
- Lu, Ming-Zhu,Lu, Ping,Xu, Yun-He,Loh, Teck-Peng
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p. 2614 - 2617
(2014/06/09)
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- A highly efficient and recyclable Fe3O4 magnetic nanoparticle immobilized palladium catalyst for the direct C-2 arylation of indoles with arylboronic acids
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A highly efficient Fe3O4 magnetic nanoparticle (MNP) immobilized palladium catalyst was prepared and applied to the direct C-2 arylation of indoles with arylboronic acids. The reactions generated the corresponding cross-coupling products in good yields. In addition, the supported catalyst with low loading (2.0 mol%) showed high stability and could be recovered and reused 8 times without significant loss of activity. The Royal Society of Chemistry 2014.
- Zhang, Lei,Li, Pinhua,Liu, Can,Yang, Jin,Wang, Min,Wang, Lei
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p. 1979 - 1988
(2014/06/24)
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- Microwave-accelerated Pd-catalyzed desulfitative direct C2-arylation of free (NH)-indoles with arylsulfinic acids
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The rapid and efficient direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a microwave-accelerated palladium-catalyzed desulfitation reaction. By using PdCl2 as a catalyst, silver acetate as an oxidant, and H2SO4 as an additive, arylsulfinic acids with both electron-donating and electron-withdrawing groups underwent desulfitative coupling with an array of free (NH)-indoles, thereby selectively providing C2-arylindoles in good yields. From C2 shining sea: The direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a Pd-catalyzed desulfitation reaction. In the presence of an oxidant and an additive, 2-arylindoles were selectively afforded in good yields. Copyright
- Miao, Tao,Li, Pinhua,Wang, Guan-Wu,Wang, Lei
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p. 3185 - 3190
(2014/01/06)
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- Gold(I) or silver catalyzed synthesis of α-indolylacrylates
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Methyl 2-acetamidoacrylate reacted with various 2-substituted indoles in the presence of catalytic amounts of AgSbF6 or AuPPh 3NTf2 to provide the corresponding methyl 2-(2-substituted-1H-indol-3-yl)acrylates.
- Pirovano, Valentina,Facoetti, Diego,Dell'Acqua, Monica,Della Fontana, Emanuela,Abbiati, Giorgio,Rossi, Elisabetta
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p. 3812 - 3815
(2013/09/02)
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- Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
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A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
- Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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supporting information
p. 8196 - 8198
(2013/09/12)
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- PROCESSES FOR PREPARING INDOLES
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Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.
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Paragraph 0092; 00101
(2013/07/05)
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- Improved indole syntheses from anilines and vicinal diols by cooperative catalysis of ruthenium complex and acid
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By developing a new and efficient dinuclear catalyst [Ru(CO) 2(Xantphos)]2 [Xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethyl-9H-xanthene], an improved synthesis of indole from vicinal diols and anilines by cooperative catalysis of ruthenium complex and p-TSA (para-toluenesufonic acid) has been demonstrated. The presented synthetic protocol allows assembling a wide range of products in an efficient manner. Comparing to the existed protocols, our indole syntheses can be achieved at lower reaction temperature, in shorter reaction time, and with improved substrate tolerance.
- Zhang, Min,Xie, Feng,Wang, Xiaoting,Yan, Fengxia,Wang, Ting,Chen, Mengmeng,Ding, Yuqiang
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p. 6022 - 6029
(2013/05/09)
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- Palladium-catalyzed direct C-2 arylation of indoles with aryl halides in aqueous medium
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A newly developed, efficient catalytic system for direct C2-arylation of indoles with aryl halides in aqueous medium under mild conditions (80 °C) is reported. These procedures are free of toxic solvents, and exhibit improved yields and high chemo- and regioselectivity. Georg Thieme Verlag KG · Stuttgart · New York.
- Lu, Guo-Ping,Cai, Chun
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p. 2992 - 2996
(2013/02/22)
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- Novel non-competitive antagonists of kainate GluK1/GluK2 receptors
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A series of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles is synthesized by Fisher or Bischler method, followed by alkylation with an appropriate alkyl or aryl halide. Two compounds exhibit non-competitive antagonism towards GluK1 and six - towards GluK2 receptor. The values of IC 50 are in micromolar range. The investigated compounds belong to the most active GluK1 non-competitive inhibitors and are the first known negative allosteric modulators of GluK2 receptor. The observed pattern of activity is rationalized by molecular modelling, in particular by construction of the pharmacophore model.
- Kaczor, Agnieszka Anna,Kronbach, Christiane,Unverferth, Klaus,Pihlaja, Kalevi,Wiinam?ki, Kirsti,Sinkkonen, Jari,Kijkowska-Murak, Urszula,Wróbel, Tomasz,Stacha, Tomasz,Matosiuk, Dariusz
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p. 891 - 898
(2013/02/22)
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- Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones
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We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.
- Wei, Ye,Deb, Indubhusan,Yoshikai, Naohiko
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supporting information; experimental part
p. 9098 - 9101
(2012/07/14)
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- NOVEL COMPOUNDS AS DIACYLGLYCEROL ACYLTRANSFERASE INHIBITORS
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This invention relates to novel compounds which are inhibitors of acyl coenzymeA: diacylglycerol acyltransferase 1 (DGAT-1), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy for the prevention or treatment of diseases related to DGAT-1 dysfunction or where modulation of DGAT-1 activity may have therapeutic benefit including but not limited to obesity, obesity related disorders, hypertriglyceridemia, hyperlipoproteinemia, chylomicronemia, dyslipidemia, non-alcoholic steatohepatitis, diabetes, insulin resistance, metabolic syndrome, hepatitis C virus infection and acne or other skin disorders.
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Page/Page column 88
(2012/12/13)
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- Ruthenium-catalyzed direct C-H bond arylations of heteroarenes
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Ruthenium-catalyzed C-H bond arylations of indoles, thiophenes, and pyrroles were accomplished in a highly chemo- and site-selective manner through the use of removable directing groups.
- Ackermann, Lutz,Lygin, Alexander V.
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supporting information; experimental part
p. 3332 - 3335
(2011/09/12)
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- Fischer indole synthesis with organozinc reagents
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Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity. Copyright
- Haag, Benjamin A.,Zhang, Zhi-Guang,Li, Jin-Shan,Knochel, Paul
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supporting information; experimental part
p. 9513 - 9516
(2011/02/24)
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