- A Friedel-Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst
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Computational calculations based on experimental results shed light on the mechanistic proposal for a Friedel-Crafts alkylation reaction between indole and nitroalkenes, catalysed by a chiral aminoindanol-derived thiourea. In our hypothesis both substrate
- Roca-Lopez, David,Marques-Lopez, Eugenia,Alcaine, Ana,Merino, Pedro,Herrera, Raquel P.
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- Gold(I)-Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
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Several group 11 metal complexes with chiral thiourea organocatalysts have been prepared and tested as organocatalysts. The promising results on the influence of metal-assisted thiourea organocatalysts in the asymmetric Friedel–Crafts alkylation of indole
- Izaga, Anabel,Herrera, Raquel P.,Gimeno, M. Concepción
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- Hydrogen Bonding Networks in Chiral Thiourea Organocatalysts: Evidence on the Importance of the Aminoindanol Moiety
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The crystal structures of four chiral thioureas, which are normally used as organocatalysts, are reported by the first time. Each compound is assembled in the crystal in a different way according to their chiral moiety in the thiourea skeleton, being depe
- Gimeno, M. Concepción,Herrera, Raquel P.
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- Thiourea-functionalized MIL-101(Cr) metal-organic framework as a hydrogen-bond-donating heterogeneous organocatalyst for the Friedel-Crafts alkylation and Biginelli reactions
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In the present paper, a functionally diverse thiourea-grafted MOF was fabricated via postsynthetic modification process through complexation of MIL-101(Cr) with pyridine containing thiourea ligand. This new modified material overcomes a significant tenden
- Mohammadian, Reza,Amini, Mostafa M.,Shaabani, Ahmad
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- Higher enantioselectivities in thiourea-catalyzed Michael additions under solvent-free conditions
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Enantioselective Michael additions catalyzed by hydrogen-bonding catalysts produce many important compounds. Solvent-free reaction conditions in a ball mill can provide an improved enantioselectivity over the reaction in solution, due to lack of disruptiv
- Hestericová, Martina,?ebesta, Radovan
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- Hydrogen-Bonding-Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water
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Metal-bound water molecules have recently been recognized as a new facet of soft Lewis acid catalysis. Herein, a chiral palladium aqua complex was constructed that enables carbon–hydrogen bonds of indoles to be functionalized efficiently. We embraced a ch
- Kitanosono, Taku,Hisada, Tomoya,Yamashita, Yasuhiro,Kobayashi, Shū
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- Design, synthesis, and pharmacological profiling of cannabinoid 1 receptor allosteric modulators: Preclinical efficacy of C2-group GAT211 congeners for reducing intraocular pressure
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Allosteric modulators of cannabinoid 1 receptor (CB1R) show translational promise over orthosteric ligands due to their potential to elicit therapeutic benefit without cannabimimetic side effects. The prototypic 2-phenylindole CB1R allosteric modulator, GAT211 (1), demonstrates preclinical efficacy in various disease models. The limited systematic structure–activity relationship (SAR) data at the C2 position of the indole ring within GAT211 invites the opportunity for further modifications to improve GAT211′s pharmacological profile while serving to amplify and variegate this library of therapeutically attractive agents. These considerations prompted this focused SAR study in which we substituted the GAT211 C2-phenyl ring with heteroaromatic substituents. The synthesized GAT211 analogs were then evaluated in vitro as CB1R allosteric modulators in cAMP and β-arrestin2 assays with CP55,940 as the orthosteric ligand. Furan and thiophene rings (15c-f and 15m) were the best-tolerated substituents at the C2 position of GAT211 for engagement with human CB1R (hCB1R). The SAR around the novel ligands reported allowed direct experimental characterization of the interaction profile of that pharmacophore with its binding domain in functional, human CB1R, thus offering guidance for accessing subsequent-generation hCB1R allosteric modulators as potential therapeutics. The most potent analog, 15d, markedly promoted orthosteric ligand binding to hCB1R. Pharmacological profiling in the GTPγS and mouse vas deferens assays demonstrated that 15d behaves as a CB1R agonist-positive allosteric modulator (ago-PAM), as confirmed electrophysiologically in autoptic neurons. In vivo, 15d was efficacious as a topical agent that significantly reduced intraocular pressure (IOP) in the ocular normotensive murine model of glaucoma. Since elevated IOP is a decisive risk factor for glaucoma and attendant vision loss, our data support the proposition that the 2-phenylindole class of CB1R ago-PAMs has therapeutic potential for glaucoma and other diseases where potentiation of CB1R signaling may be therapeutic.
- Garai, Sumanta,Schaffer, Peter C.,Laprairie, Robert B.,Janero, David R.,Pertwee, Roger G.,Straiker, Alex,Thakur, Ganesh A.
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- Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts
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A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumber
- Dündar, Esra,Tanyeli, Cihangir
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- A robust heterogeneous Co-MOF catalyst in azide-alkyne cycloaddition and Friedel-Crafts reactions as well as hydrosilylation of alkynes
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Organic reactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmentally friendly features and potential catalyst recyclability. A robust Co(ii)-MOF {[Co2(l-mac)(4,4-bpt)(H2O)]·3.5H2O}n (1) and its enantiomer {[Co2(d-mac)(4,4-bpt)(H2O)]·3.5H2O}n (2) (l/d-mac = basic forms of l/d-malic acid, 4,4-Hbpt = 3,5-di(pyridin-4-yl)-4H-1,2,4-triazole) have been gram-scale prepared under solvothermal conditions. Structural analysis reveals that mac manages Co(ii) ions to form 1-D chains, which are further extended via 4,4-bpt connectors into a noninterpenetrating 3D framework architecture. It was found that 1 can be as a heterogeneous catalyst for multiple organic reactions, such as azide-alkyne cycloaddition and Friedel-Crafts reactions with good isolated yields and good recycle runs (at least five times without substantial degradation). Additionally, 1 can promote hydrosilylation of alkynes under harsh conditions with moderate yield. This journal is
- Wu, Tai-Xue,Jia, Jun-Song,Luo, Wei,Bian, He-Dong,Tang, Hai-Tao,Pan, Ying-Ming,Huang, Fu-Ping
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supporting information
p. 872 - 880
(2021/01/25)
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- Organo-Polyoxometalate-Based Hydrogen-Bond Catalysis
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Several urea-inserted organo-polyoxometalates (POMs) derived from polyoxotungstovanadate [P2V3W15O61]9? were prepared. The insertion of the carbonyl into the polyoxometallic framework activates the ur
- Vilona, Debora,Lelli, Moreno,Dumont, Elise,Lac?te, Emmanuel
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supporting information
p. 17761 - 17764
(2021/11/10)
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- Calix[6]arene-based Br?nsted acids for molecular recognition and catalysis
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We report the synthesis of a versatile trifluoromethylsulfonamide calix[6]arene derivative with Br?nsted acid features which can influence both molecular recognition and catalytic application. Indeed, in low polarity media, the trifluoromethyl-containing
- Cera, Gianpiero,Cester Bonati, Federica,Bazzoni, Margherita,Secchi, Andrea,Arduini, Arturo
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p. 1546 - 1554
(2021/03/01)
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- A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones
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A general strategy for the synthesis of indolyl cyclobutanones via a tandem Bronsted acid catalyzed 2-hydroxycyclobutanone activation-indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.
- Porcu, Stefania,Rodriguez, Carla Aira,Frongia, Angelo,Secci, Francesco
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supporting information
p. 925 - 932
(2020/12/14)
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- 2-[1-(Dimethylamino)ethyl]ferrocenylphosphinic acid as an organocatalyst of Michael and Friedel—Crafts reactions
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Racemic 2-[1-(dimethylamino)ethyl]ferrocenylphosphinic acid was tested as an organocatalyst in the Michael and Friedel—Crafts reactions. The use of this zwitterion provides 78% conversion in the Michael reaction between cyclohexanone and β-nitrostyrene, a
- Gilmanova, L. H.,Miluykov, V. A.,Shekurov, R. P.,Zagidullin, A. A.
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p. 1415 - 1417
(2021/08/10)
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- New 1D chiral Zr-MOFs based on in situ imine linker formation as catalysts for asymmetric C–C coupling reactions
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A novel chiral diimine Zr-MOF (DUT-136, DUT - Dresden University of Technology) is synthesized in a one-pot reaction from ZrCl4, 4-formylbenzoic acid, and (R,R)-1,2-diphenylethylenediamine as an enantiopure core. Inspired by the versatile chemi
- Bon, Volodymyr,Ehrling, Sebastian,Kaskel, Stefan,Nguyen, Khoa D.,Senkovska, Irena
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p. 106 - 116
(2020/05/01)
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- Rose bengal as photocatalyst: Visible light-mediated Friedel-Crafts alkylation of indoles with nitroalkenes in water
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A novel and facile visible-light-mediated alkylation of indoles and nitroalkenes has been developed. In this protocol, rose bengal acts as a photosensitizer, and environmentally benign water was used as the green and efficient reaction medium. Indoles rea
- Yu, Zong-Yi,Zhao, Jing-Nan,Yang, Fan,Tang, Xiao-Fei,Wu, Yu-Feng,Ma, Cun-Fei,Song, Bo,Yun, Lei,Meng, Qing-Wei
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p. 4825 - 4831
(2020/02/13)
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- Influence of oxophilic behavior of UiO-66(Ce) metal–organic framework with superior catalytic performance in Friedel-Crafts alkylation reaction
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In recent years, one of the analogous metal organic frameworks (MOFs) with UiO-66(Zr) topology receiving wider attention is UiO-66(Ce), which exhibits interesting properties and high thermal and chemical stability. Hence, in the present work, UiO-66(Ce) i
- Nagarjun, Nagarathinam,Concepcion, Patricia,Dhakshinamoorthy, Amarajothi
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- B(C6F5)3-Catalyzed Conjugate Addition Reactions: Addition of C–H Aromatics as Nucleophiles to Nitroalkenes
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A mild and efficient B(C6F5)3-catalyzed conjugate addition of N, N-dialkylanilines to aromatic nitroalkenes is reported. The catalyst shows excellent catalytic activity and very broad substrate scopes for the alkylation re
- Qi, Liang
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p. 169 - 173
(2020/03/30)
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- Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes
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We describe the application of a novel family of trisulfonamide (TSA) calix[6]arenes in general acid catalysis. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles to nitroalkene derivati
- Arduini, Arturo,Balestri, Davide,Bazzoni, Margherita,Cera, Gianpiero,Marchiò, Luciano,Secchi, Andrea
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supporting information
p. 6241 - 6246
(2020/09/07)
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- Friedel–Crafts reaction of electron-rich (het)arenes with nitroalkenes
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The Friedel–Crafts reaction between electron-rich (het)arenes and β-nitrostyrenes under MgI2 or Ca(NTf2)2 catalysis affords 1-(het)aryl-2-nitro-1-phenylethanes in yields up to 94%.
- Feofanov, Mikhail N.,Averin, Alexei D.,Beletskaya, Irina P.
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p. 138 - 139
(2019/04/25)
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- Charge-enhanced thiourea catalysts as hydrogen bond donors for Friedel?Crafts Alkylations
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Charge-enhanced catalysis has emerged as a powerful alternative to the mainstream use of neutral catalysis. With this in mind, we report a catalytic Friedel?Crafts alkylation method catalyzed by a charged thiourea incorporating a cationic cyclopropenium m
- Smajlagic, Ivor,Carlson, Brenden,Rosano, Nicholas,Foy, Hayden,Dudding, Travis
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- Electrostatically enhanced phosphoric acids and their applications in asymmetric friedel-crafts alkylations
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A series of electrostatically enhanced phosphoric acid catalysts were synthesized and studied. These compounds possess two positively charged N-octylpyridinium or triarylphosphonium ion centers at the 3,3′-positions of the (R)-BINOL backbone to enhance re
- Ma, Jie,Kass, Steven R.
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p. 11125 - 11134
(2019/09/10)
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- Kinetic and Binding Studies Reveal Cooperativity and Off-Cycle Competition for H-Bonding Catalysis with Silsesquioxane Silanols
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The catalytic activity, kinetics, and quantification of H-bonding ability of incompletely condensed polyhedral oligomeric silsesquioxane (POSS) silanols are reported. POSS-triols, a homogeneous model for vicinal silica surface sites, exhibit enhanced H-bo
- Jagannathan, Jake R.,Diemoz, Kayla M.,Targos, Karina,Fettinger, James C.,Franz, Annaliese K.
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supporting information
p. 14953 - 14958
(2019/11/13)
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- Identification of cb1 receptor allosteric sites using force-biased mmc simulated annealing and validation by structure-activity relationship studies
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Positive allosteric modulation of the cannabinoid 1 receptor (CB1R) has demonstrated distinct therapeutic advantages that address several limitations associated with orthosteric agonism and has opened a promising therapeutic avenue for further drug development. To advance the development of CB1R positive allosteric modulators, it is important to understand the molecular architecture of CB1R allosteric site(s). The goal of this work was to use Force-Biased MMC Simulated Annealing to identify binding sites for GAT228 (R), a partial allosteric agonist, and GAT229 (S), a positive allosteric modulator (PAM) at the CB1R. Our studies suggest that GAT228 binds in an intracellular (IC) TMH1-2-4 exosite that would allow this compound to act as a CB1 allosteric agonist as well as a CB1 PAM. In contrast, GAT229 binds at the extracellular (EC) ends of TMH2/3, just beneath the EC1 loop. At this site, this compound can act as CB1 PAM only. Finally, these results were successfully validated through the synthesis and biochemical evaluation of a focused library of compounds.
- Hurst, Dow P.,Garai, Sumanta,Kulkarni, Pushkar M.,Schaffer, Peter C.,Reggio, Patricia H.,Thakur, Ganesh A.
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supporting information
p. 1216 - 1221
(2019/08/27)
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- Design of a Primary-Amide-Functionalized Highly Efficient and Recyclable Hydrogen-Bond-Donating Heterogeneous Catalyst for the Friedel-Crafts Alkylation of Indoles with β-Nitrostyrenes
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A primary-amide-functionalized metal organic framework, {[Zn2(2-BQBG)(BDC)2]·10H2O}n (1) (in which 2-BQBG = 2,2′-(butane-1,4-diylbis((quinolin-2-ylmethyl)azanediyl))diacetamide and BDC = 1,4-benzenedicarboxylate
- Markad, Datta,Mandal, Sanjay K.
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p. 3165 - 3173
(2019/03/26)
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- Highly Active Urea-Functionalized Zr(IV)-UiO-67 Metal-Organic Framework as Hydrogen Bonding Heterogeneous Catalyst for Friedel-Crafts Alkylation
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A new Zr(IV)-based UiO-67 metal-organic framework (1) was prepared with urea-functionalized biphenyl-4,4′-dicarboxylic acid (BPDC-urea) as the linker using conventional solvothermal technique and thoroughly characterized using X-ray powder diffraction (XR
- Das, Aniruddha,Anbu, Nagaraj,Sk, Mostakim,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
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p. 5163 - 5172
(2019/04/25)
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- The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives
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Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.
- Satyam, Killari,Murugesh,Suresh, Surisetti
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supporting information
p. 5234 - 5238
(2019/06/07)
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- Catalytic and conductivity studies in two dimensional coordination polymers built with a thiazole based ligand
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The employment of the commercial available organic ligand 2-mercapto-4-methyl-5-thiazoleacetic acid (H2L) in Zn and Cd chemistry yields two-dimensional (2D) coordination polymers (CPs) with pseudopolymorphic character. Thermal, catalytic and co
- Kumar, Prashant,Lymperopoulou, Smaragda,Loukopoulos, Edward,Matsuda, Wakana,Kourkoumelis, Nikolaos,Seki, Shu,Kostakis, George E.
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- Preparation of chitosan-supported urea materials and their application in some organocatalytic procedures
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An efficient and mild procedure was developed for the preparation of three chitosan-supported ureas containing electron-withdrawing groups. These catalysts were characterized and employed as organocatalysts in different transformations, including the enan
- de Gonzalo, Gonzalo,Franconetti, Antonio,Fernández, Rosario,Lassaletta, José M.,Cabrera-Escribano, Francisca
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p. 365 - 374
(2018/07/25)
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- Preparation of a chiral Pt12 tetrahedral cage and its use in catalytic Michael addition reaction
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The reaction of chiral cis-[(1S,2S)-dch]Pt(NO3)2 (M) [where (1S,2S)-dch = (1S,2S)-1,2-diaminocyclohexane] with a hexadentate ligand (L) in 3:1 stoichiometric ratio yielded a [12+4] self-assembled chiral M12L4 mo
- Bhat, Imtiyaz Ahmad,Devaraj, Anthonisamy,Howlader, Prodip,Chi, Ki-Whan,Mukherjee, Partha Sarathi
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supporting information
p. 4814 - 4817
(2018/05/23)
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- Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalyst
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The hydrogen bond donating ability of 1,8-naphthalenediol was investigated via a series of 1H, 13C, and 31P NMR experiments. Complexation studies using triphenylphosphine oxide and cyclohexanone as hydrogen bond acceptors
- Turkmen, Yunus Emre
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p. 1398 - 1407
(2018/10/23)
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- Bottom-Up Assembly of a Highly Efficient Metal-Organic Framework for Cooperative Catalysis
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In this study, we demonstrate a bottom-up assembly of a monomeric copper complex and a two-dimensional (2-D) heterometallic metal-organic framework (MOF) from a carboxylate-functionalized tridentate Schiff base ligand and metal ions. The obtained 2-D MOF
- Li, Changda,Tang, Haitong,Fang, Yu,Xiao, Zhifeng,Wang, Kunyu,Wu, Xiang,Niu, Helin,Zhu, Chengfeng,Zhou, Hong-Cai
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supporting information
p. 13912 - 13919
(2018/10/20)
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- Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents
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An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.
- Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
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p. 10314 - 10317
(2018/03/26)
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- An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions
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This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.
- Chiu, Chien-Cheng,Chiu, Hui-Tzu,Lee, Dong-Sheng,Lu, Ta-Jung
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p. 26407 - 26415
(2018/08/04)
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- TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
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TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.
- Firouzabadi, Habib,Iranpoor, Naser,Farahi, Soghra
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p. 317 - 323
(2018/02/06)
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- Improved MOF nanoparticle recovery and purification using crosslinked PVDF membranes
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Crosslinked PVDF-membranes are demonstrated to offer a viable alternative for centrifugation in the preparation of MOF-particles, thus realising new opportunities at lab-scale and continuous production at large-scale. The membranes combine extreme-pH with
- Van Goethem, Cédric,Mertens, Matthias,Cirujano, Francisco G.,Seo, Jin W.,De Vos, Dirk,Vankelecom, Ivo F. J.
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supporting information
p. 7370 - 7373
(2018/07/06)
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- 2D-2D Nanocomposite of MoS2-Graphitic Carbon Nitride as Multifunctional Catalyst for Sustainable Synthesis of C3-Functionalized Indoles
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A nanocomposite of two-dimensional MoS2 supported on graphitic C3N4 nanosheets has been prepared by a facile ultrasonication method followed by demonstrating its ability to catalyze the synthesis of several indole derivatives. The as-prepared nanocomposite catalyst was characterized in detail by using different microscopic and spectroscopic techniques to understand its structure and physicochemical properties. Subsequently, this nanocomposite catalyst was used as a heterogeneous multifunctional catalyst to synthesize several C3-functionalized indoles in the aqueous medium. The employed strategy also provided very good catalyst recyclability and versatility for the synthesis of various precursors of medicinally significant indoles, such as serotonin, melatonin, and various β-carboline alkaloids. In addition, a natural product derivate has been prepared on the gram-scale by using this methodology. Furthermore, high atom economy (100 %) and lower E-factor (0.042) makes this strategy a sustainable approach for the synthesis of C3-functionalized indoles.
- Bahuguna, Ashish,Kumar, Ashwani,Kumar, Suneel,Chhabra, Tripti,Krishnan, Venkata
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p. 3121 - 3132
(2018/07/29)
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- Reaction Progress Kinetics Analysis of 1,3-Disiloxanediols as Hydrogen-Bonding Catalysts
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1,3-Disiloxanediols are effective hydrogen-bonding catalysts that exhibit enhanced activity relative to silanediols and triarylsilanols. The catalytic activity for a series of 1,3-disiloxanediols, including naphthyl-substituted and unsymmetrical siloxanes, has been quantified and compared relative to other silanol and thiourea catalysts using the Friedel Crafts addition of indole to trans-β-nitrostyrene. An in-depth kinetic study using reaction progress kinetic analysis (RPKA) has been performed to probe the catalyst behavior of 1,3-disiloxanediols. The data confirm that the disiloxanediol-catalyzed addition reaction is first order in catalyst over all concentrations studied with no evidence of catalyst self-association. 1,3-Disiloxanediols proved to be robust and recoverable catalysts with no deactivation under reaction conditions. No product inhibition is observed, and competitive binding studies with nitro-containing additives suggest that 1,3-disiloxanediols bind weakly to nitro groups but are strongly activating for catalysis.
- Diemoz, Kayla M.,Hein, Jason E.,Wilson, Sean O.,Fettinger, James C.,Franz, Annaliese K.
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supporting information
p. 6738 - 6747
(2017/07/15)
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- Friedel–Crafts Alkylation of Indoles with Nitroalkenes through Hydrogen-Bond-Donating Metal–Organic Framework
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Urea-derived hydrogen-bond-donating (HBD) catalysts are good catalysts for organic transformations. Usually, urea derivatives undergo self-recognition and aggregation during homogeneous catalytic processes. To avoid this, a new approach involving the inco
- Rao, Purna Chandra,Mandal, Sukhendu
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p. 1172 - 1176
(2017/04/14)
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- The Friedel-Crafts Reaction of Indoles with Michael Acceptors Catalyzed by Magnesium and Calcium Salts
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Friedel-Crafts alylation of indole and its derivatives with a variety of electron-deficient alkenes catalyzed by Mg and Ca salts has been studied. The dependence of the results on the nature of the starting olefins, substituents on indole, and Michael acc
- Feofanov, Mikhail N.,Anokhin, Maxim V.,Averin, Alexei D.,Beletskaya, Irina P.
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p. 5045 - 5058
(2017/10/06)
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- Selective One-Pot Two-Step C?C Bond Formation using Metal–Organic Frameworks with Mild Basicity as Heterogeneous Catalysts
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Copper-ion-exchanged nickel pyrazolate frameworks behave as selective heterogeneous catalysts for the one-pot, two-step (Henry reaction/Michael type addition) synthesis of neuroactive pharmaceutical intermediates starting from nitromethane and benzaldehyde. Tuning the basicity of multifunctional metal–organic framework catalysts through ion exchange with copper(II) cations allows the tandem C?C bond-forming process to be selectively directed towards the desired pharmaceutical intermediate.
- Cirujano, Francisco G.,López-Maya, Elena,Rodríguez-Albelo, Marleny,Barea, Elisa,Navarro, Jorge A. R.,De Vos, Dirk E.
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p. 4019 - 4023
(2017/11/15)
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- Compound and its preparation method and application
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The invention provides a compound and a preparation method therefore and application thereof. The compound is a compound shown in a formula I or an enantiomer, a diastereoisomer, raceme, pharmaceutically acceptable salt, a crystalline hydrate or a solvate of the compound, wherein R1 is optionally substituted phenyl, R2 is p-methylphenyl and X is C or N. The compound can be used for treating cancer related diseases. The formula I is shown in the description.
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- Water-soluble (salicyladimine)2Cu complex as an efficient and renewable catalyst for Michael addition of indoles to nitroolefins in water
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An efficient and environmentally friendly protocol has been demonstrated for water-soluble (salicyladimine)2Cu complex-catalyzed Michael addition of indoles to nitroolefins in water at 30 °C. A variety of substituted indoles and β-nitrostyrenes could be worked well to provide the title products in 81–97% yields. Moreover, the catalyst can be reused directly at least for four times without significantly decreasing activity.
- Jiang, Haojie,Zhang, Jie,Xie, Jianwei,Liu, Ping,Xue, Mei
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supporting information
p. 211 - 216
(2017/01/22)
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- Electrostatically enhanced phosphoric acids: A tool in Br?nsted acid catalysis
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A novel type of phosphoric acid catalyst with enhanced reactivity is reported. These compounds possess one or two positively charged centers which electrostatically activate them. This is illustrated in several bond-forming transformations including Friedel-Crafts and Diels-Alder reactions as well as a ring-opening polymerization. Rate accelerations corresponding to orders of magnitude are observed.
- Ma, Jie,Kass, Steven R.
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supporting information
p. 5812 - 5815
(2016/11/29)
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- The synthesis of substituted amino[2.2]paracyclophanes
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Two methodologies for the formation of substituted amino[2.2]paracyclophane derivatives were developed. The first involves the direct amination of bromo[2.2]paracyclophanes with sodium azide. This permits the synthesis of simple mono- and disubstituted de
- Jayasundera, Krishanthi P.,Kusmus, Disra?li N. M.,Deuilhé, Lise,Etheridge, Leonie,Farrow, Zane,Lun, David J.,Kaur, Gurpreet,Rowlands, Gareth J.
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p. 10848 - 10860
(2016/12/06)
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- Temperature Dual Enantioselective Control in a Rhodium-Catalyzed Michael-Type Friedel–Crafts Reaction: A Mechanistic Explanation
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By changing the temperature from 283 to 233 K, the S (99 % ee) or R (96 % ee) enantiomer of the Friedel–Crafts (FC) adduct of the reaction between N-methyl-2-methylindole and trans-β-nitrostyrene can be obtained by using (SRh,RC)-[(η5-C5Me5)Rh{(R)-Prophos}(H2O)][SbF6]2as the catalyst precursor. This catalytic system presents two other uncommon features: 1) The ee changes with reaction time showing trends that depend on the reaction temperature and 2) an increase in the catalyst loading results in a decrease in the ee of the S enantiomer. Detection and characterization of the intermediate metal–nitroalkene and metal–aci-nitro complexes, the free aci-nitro compound, and the FC adduct-complex, together with solution NMR measurements, theoretical calculations, and kinetic studies have allowed us to propose two plausible alternative catalytic cycles. On the basis of these cycles, all the above-mentioned observations can be rationalized. In particular, the reversibility of one of the cycles together with the kinetic resolution of the intermediate aci-nitro complexes account for the high ee values achieved in both antipodes. On the other hand, the results of kinetic measurements explain the unusual effect of the increment in catalyst loading.
- Méndez, Isabel,Rodríguez, Ricardo,Polo, Víctor,Passarelli, Vincenzo,Lahoz, Fernando J.,García-Ordu?a, Pilar,Carmona, Daniel
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supporting information
p. 11064 - 11083
(2016/07/28)
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- Baker's yeast as an efficient biocatalyst for regioselective 1,4-conjugate addition of indoles to nitroolefins in aqueous medium
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The 1,4-conjugate addition of indoles to nitroolefins was efficiently carried out in aqueous media using baker's yeast as a biocatalyst at room temperature. The merits of the present method are operational simplicity, easy workup, utilization of an inexpensive catalyst, free from hazardous organic solvents and good yields of products. The generality of this method was demonstrated by synthesizing an array of diverse 3-substituted indole derivatives and could be extended for dialkylation of 1,4-bis-(2-nitrovinyl)benzene.
- Mane, Ananda,Lohar, Trushant,Salunkhe, Rajashri
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supporting information
p. 2341 - 2346
(2016/05/19)
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- Oxidative organophotoredox catalysis: A regioselective synthesis of 2-nitro substituted imidazopyridines and 3-substituted indoles, initiated by visible light
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We have established a mild, metal-free, one pot, visible light-catalyzed procedure for a highly regioselective synthesis of 2-nitro-3-arylimidazo [1,2-a] pyridines via nitroalkene and 2-aminopyridine under an open atmosphere involving a photoredox catalys
- Singh, Jagdamba,Yadav, Snehlata,Srivastava, Madhulika,Rai, Pratibha,Tripathi, Bhartendu Pati,Mishra, Anu,Singh, Jaya
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supporting information
p. 9694 - 9701
(2016/11/11)
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- Lewis Acid Activation of a Hydrogen Bond Donor Metal-Organic Framework for Catalysis
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A new metal-organic framework (MOF) composed of urea-containing tetracarboxylate struts was synthesized, and its hydrogen bonding capabilities were evaluated. The catalytic performance of this heterogeneous framework is enhanced through preactivation with silyl Lewis acids, leading to Friedel-Crafts reaction rates greater than those of common homogeneous hydrogen bond donors.
- Hall, Edward A.,Redfern, Louis R.,Wang, Michael H.,Scheidt, Karl A.
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p. 3248 - 3252
(2016/07/06)
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- Design and synthesis of squaramide-based MOFs as efficient MOF-supported hydrogen-bonding organocatalysts
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Herein, we utilize a new, squaramide-based ligand, combined with a postsynthetic exchange (PSE) synthetic approach to prepare a series of Cu(ii)-squaramide MOFs that are active catalysts for the Friedel-Crafts reaction.
- Zhang, Xiaoping,Zhang, Zhenjie,Boissonnault, Jake,Cohen, Seth M.
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supporting information
p. 8585 - 8588
(2016/07/14)
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- Michael addition of indoles to β-nitrostyrenes catalyzed by HY zeolite under solvent-free conditions
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Michael addition of indoles to β-nitrostyrenes is reported using HY zeolite as catalyst under mild reaction conditions. This methodology allows the synthesis of various indole derivatives in good to high yields at 50 °C under solvent-free conditions. The short reaction time and achieving high yield of the desired products are the main advantages of the present work. The catalyst can be easily recovered and reused for six successive runs without considerable changes in yields. This Michael addition catalyzed by HY zeolite is operationally simple and can be considered as a greener protocol as it avoids the use of corrosive acids and toxic reagents.
- Jeganathan, Mariappan,Kanagaraj, Kuppusamy,Dhakshinamoorthy, Amarajothi,Pitchumani, Kasi
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supporting information
p. 2061 - 2064
(2015/03/18)
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- Strong Lewis acids of air-stable binuclear triphenylantimony(V) complexes and their catalytic application in C-C bond-forming reactions
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Two air-stable novel Lewis acids of triphenylantimony(V) pentafluorbezenesulfonates (2) and perfluorooctanesulfonates (3) were successfully synthesized and characterized. X-ray studies and thermo-gravimetric analysis found that these complexes showed high anti-hydrolyzability and thermal stability. The high catalytic activity and excellent recyclability of these complexes were achieved in the Michael addition reaction and the allylation reaction. On account of their stability, storability, as well as catalytic efficiency, these complexes should find a broad range of utility in organic synthesis.
- Li, Ningbo,Qiu, Renhua,Zhang, Xiaohong,Chen, Yun,Yin, Shuang-Feng,Xu, Xinhua
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p. 4275 - 4281
(2015/06/08)
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