- Synthesis method of monosubstituted or disubstituted furan derivatives
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The invention relates to the field of medicine synthesis, and provides a synthesis method of monosubstituted or disubstituted furan derivatives, wherein the synthesis method can be used for synthesizing various furan derivatives with different substituent groups and has high flexibility. According to the synthesis method of the monosubstituted or disubstituted furan derivatives, 5-hydroxymethyl-[delta]2-isoxazoline derivative is used as a raw material in an acidic solvent, and the monosubstituted or disubstituted furan derivatives are synthesized in one step under the action of a metal reducing agent; and according to the method, the furan derivatives with different substituent groups can be synthesized by adopting the 5-hydroxymethyl-[delta]2-isoxazoline derivatives with different substituent groups, high flexibility is achieved, the technical scheme is simple in step and mild in reaction condition, synthesis of the furan derivatives can be achieved through a one-pot method, the reaction yield is high, and large-scale production is facilitated.
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Paragraph 0042-0044
(2021/09/29)
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- Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex
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The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.
- Paul, Swagata,Das, Kanak Kanti,Manna, Samir,Panda, Santanu
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supporting information
p. 1922 - 1927
(2020/02/04)
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- Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds
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A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.
- Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saravanan, Subramanian,Saritha, Rajendhiran
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supporting information
p. 2510 - 2515
(2020/04/15)
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- Orthogonal Nanoparticle Catalysis with Organogermanes
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Although nanoparticles are widely used as catalysts, little is known about their potential ability to trigger privileged transformations as compared to homogeneous molecular or bulk heterogeneous catalysts. We herein demonstrate (and rationalize) that nanoparticles display orthogonal reactivity to molecular catalysts in the cross-coupling of aryl halides with aryl germanes. While the aryl germanes are unreactive in LnPd0/LnPdII catalysis and allow selective functionalization of established coupling partners in their presence, they display superior reactivity under Pd nanoparticle conditions, outcompeting established coupling partners (such as ArBPin and ArBMIDA) and allowing air-tolerant, base-free, and orthogonal access to valuable and challenging biaryl motifs. As opposed to the notoriously unstable polyfluoroaryl- and 2-pyridylboronic acids, the corresponding germanes are highly stable and readily coupled. Our mechanistic and computational studies provide unambiguous support of nanoparticle catalysis and suggest that owing to the electron richness of aryl germanes, they preferentially react by electrophilic aromatic substitution, and in turn are preferentially activated by the more electrophilic nanoparticles.
- Fricke, Christoph,Sherborne, Grant J.,Funes-Ardoiz, Ignacio,Senol, Erdem,Guven, Sinem,Schoenebeck, Franziska
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supporting information
p. 17788 - 17795
(2019/11/13)
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- Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles
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The unprecedented Trametes versicolor laccase/TEMPO-catalyzed aromatization of 2,5-dihydrofurans to furans is described. A variety of furan derivatives have been synthesized in moderate to high conversions (21-99%) and yields (20-76%) under mild reaction
- Risi, Caterina,Zhao, Fei,Castagnolo, Daniele
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p. 7264 - 7269
(2019/10/02)
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- Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles
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Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.
- Zorba, Leandros,Kidonakis, Marios,Saridakis, Iakovos,Stratakis, Manolis
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p. 5552 - 5555
(2019/08/01)
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- Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C?C Bond Formations under Visible Light
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Metal-free and photocatalytic radical-mediated aromatic C?C bond formations offer a promising alternative pathway to the conventional transition metal-catalyzed cross-coupling reactions. However, the formation of aryl radicals from common precursors such as aryl halides is highly challenging due to their extremely high reductive potential. Here, we report a structural design strategy of donor-acceptor-type organic photocatalysts for visible light-driven C?C bond formations through the reductive dehalogenation of aryl halides. The reduction potential of the photocatalysts could be systematically aligned to be ?2.04 V vs. SCE via a simple heteroatom engineering of the donor-acceptor moieties. The high reductive potential of the molecular photocatalyst could reduce various aryl halides into aryl radicals to form the C?C bond with heteroarenes. The designability of the molecular photocatalyst further allowed the synthesis of a high LUMO (lowest unoccupied molecular orbital) polymer photocatalyst by a self-initiated free radical polymerization without compromising its LUMO level. (Figure presented.).
- Wang, Lei,Byun, Jeehye,Li, Run,Huang, Wei,Zhang, Kai A. I.
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p. 4312 - 4318
(2018/10/02)
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- Facile C–H arylation using catalytically active terminal sulfurs of 2 dimensional molybdenum disulfide
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The first methodology of C–H arylation of heteroarene via 2D transition metal dichalcogenides that have catalytically active edge functional groups was described. The terminal sulfur groups could effectively catalyze a formation of an azo-linked intermediate with aryl diazonium salts, leading to produce heteroarenes with good yields. This novel methodology using bulk 2D transition metal dichalcogenides that have catalytically active edge functional groups can apply for various reactions to achieve C–C bond formation in the fields of heterogeneous catalysis that is easily separable, highly reusable, and inexpensive method.
- Hwang, Eunhee,Mi Lee, Sae,Bak, Sora,Min Hwang, Hee,Kim, Hyunjung,Lee, Hyoyoung
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supporting information
p. 3969 - 3973
(2018/10/02)
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- Manganese-Catalyzed Aerobic Heterocoupling of Aryl Grignard Reagents
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An improved protocol has been developed for the MnCl2-catalyzed cross-coupling reaction of two arylmagnesium bromides under dioxygen. The reaction was achieved by using the Grignard reagents in a 2:1 ratio and 20 % of MnCl2. Very good yields of the heterocoupling product were obtained when the limiting Grignard reagent underwent little homocoupling under the reaction conditions. Arylmagnesium bromides that contain p-methoxy, p-(dimethylamino), p-fluoro, and p-chloro substituents were shown to afford high product yields in the cross-coupling reactions with a variety of substituted aryl Grignard reagents. Heterocyclic Grignard reagents, on the other hand, were less effective substrates for this transformation because of the rapid homocoupling of these reagents under the reaction conditions.
- Ghaleshahi, Hajar Golshahi,Antonacci, Giuseppe,Madsen, Robert
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p. 1331 - 1336
(2017/03/23)
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- Synthesis of 2,5-Disubstituted Furans from Sc(OTf)3 Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones
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A convenient synthesis of 2,5-disubstituted furan was developed by employing donor-acceptor oxiranes in a new reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,5-disubstituted furans are obtained in moderate to good yields under mild reaction conditions. The scope of the reaction is quite decent, allowing for the synthesis of disubstituted furans having aryl and heteroaromatic groups.
- Mondal, Keshab,Pan, Subhas Chandra
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p. 4415 - 4421
(2017/04/27)
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- Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor
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Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.
- Fabry, David C.,Ho, Yee Ann,Zapf, Ralf,Tremel, Wolfgang,Panth?fer, Martin,Rueping, Magnus,Rehm, Thomas H.
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supporting information
p. 1911 - 1918
(2017/06/09)
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- Gram-scale synthesis of aligned C3N4-polypyrrole heterojunction aerogels with tunable band structures as efficient visible and near infrared light-driven metal-free photocatalysts
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The assembly of aligned porous materials from simple building blocks is of widespread interest for engineering materials with enhanced and synergistic properties. To date, however, how to develop 3D heterojunction aerogels with aligned porosity based on 2D semiconductor materials and 1D conducting polymers for solar energy conversion in the visible and near-infrared (NIR) light region remains a significant challenge. Here a new class of gram-scale 3D aligned heterojunction aerogels of polypyrrole (PPy)/C3N4 nanosheets (NSs) were designed and synthesized by directional freezing of polypyrrole (PPy)/polyvinyl alcohol (PVA) and C3N4 NS aqueous suspension. The synthesis of aligned C3N4-PPy heterojunction aerogels can be achieved on a large scale. The formed aerogel expresses stable and uniform dispersion of the two building blocks, long-range channel aligned structures along the whole monolithic sample, and additional special complementary optical properties between PPy and C3N4 NSs. Based on the above unique structure and optical properties, this novel metal-free heterojunction aerogel exhibits excellent photocatalytic activity and long-term stability for direct arylation of heteroaromatics under visible and near infrared (NIR) light irradiation at room temperature, far exceeding those of the single- and two-component systems. Our work therefore not only provides a new approach to obtain aligned heterojunction aerogels based on metal free semiconductors but also paves a way to develop gram-scale aerogels as a new type of highly efficient visible and NIR light induced heterogeneous photocatalyst.
- Liu, Jian,Wang, Hao,Bai, Jinwei,Li, Tianrong,Yang, Yanmei,Peng, Yong,Wang, Baodui
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p. 24920 - 24928
(2017/12/15)
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- Sodium Chloride Catalyzed Regioselective Trifluoromethylthiolation of Furans
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Here, we report the catalytic trifluoromethylthiolation of furans employing sodium chloride as an inexpensive, abundant and ecologically friendly catalyst. The developed method exhibits perfect regioselectivity and a high functional group tolerance. Furth
- Ernst, Johannes B.,Rakers, Lena,Glorius, Frank
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supporting information
p. 260 - 268
(2016/12/24)
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- Interface coassembly of mesoporous MoS2 based-frameworks for enhanced near-infrared light driven photocatalysis
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The three-dimensional porous Fe3O4@Cu2-xS-MoS2 framework is reported for the first time. The as-prepared 3D framework exhibits good structural stability, high surface area, enhanced adsorption capacity to substrates, and strong absorption in the NIR range. As a result, such hybrid frameworks exhibit excellent NIR-light photocatalytic activity and stable cycling for the direct arylation of heteroaromatics at room temperature.
- Zhi, Lihua,Zhang, Haoli,Yang, Zhengyin,Liu, Weisheng,Wang, Baodui
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supporting information
p. 6431 - 6434
(2016/05/24)
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- Fast and efficient 18F-labeling by [18F]fluorophenylazocarboxylic esters
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Introduction of [18F]fluoride ion into the aromatic core of phenylazocarboxylic esters was achieved in only 30 seconds, with radiochemical yields of up to 95% (85(±10) %). For labeling purposes, the resulting 18F-substituted azoester can be further converted in radical-arylation reactions to give biaryls, or in substitutions at its carbonyl unit to produce azocarboxamides.
- Fehler, Stefanie K.,Maschauer, Simone,Hcfling, Sarah B.,Bartuschat, Amelie L.,Tschammer, Nuska,Hubner, Harald,Gmeiner, Peter,Prante, Olaf,Heinrich, Markus R.
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supporting information
p. 370 - 375
(2014/04/03)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 178
(2012/09/21)
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- IrCl3 or FeCl3-catalyzed convenient synthesis of 3-hydroxyphthalates
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IrCl3·3H2O or FeCl3-catalyzed convenient synthesis of 3-hydroxyphthalates has been achieved by a Diels-Alder reaction of furans with dimethyl acetylenedicarboxylate, followed by ring-opening aromatization reaction of the D
- Shinohara, Hiroyuki,Sonoda, Motohiro,Atobe, Shingo,Masuno, Haruna,Ogawa, Akiya
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supporting information; experimental part
p. 6238 - 6241
(2011/12/14)
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- Synthesis of 2-substituted furans by iron- and palladium-catalyzed coupling reactions
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The synthesis of 2-substituted furans via palladium- and iron-catalyzed coupling utilizing 2-bromofuran is described. Whereas palladium-catalyzed Suzuki coupling effectively provided the corresponding aryl furans, little or no product was obtained by palladium-catalyzed coupling with various alkyl nucleophiles. Iron-catalyzed coupling proved effective for the synthesis of primary and secondary alkyl furans in modest yields and aryl furans in low yields. Georg Thieme Verlag Stuttgart New York.
- Haner, Jamie,Jack, Kelsey,Nagireddy, Jaipal,Raheem, Mohammed Abdul,Durham, Robin,Tam, William
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experimental part
p. 731 - 738
(2011/04/24)
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- New synthesis of furans: The rhodium-catalysed carbonylative addition of arylboronic acids to propargylic alcohols/cyclisation sequence
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The rhodium-catalysed carbonylative addition of arylboronic acids to propargylic alcohols yields gamma-hydroxy enones that are readily cyclised through a dehydration step to the corresponding furan analogues. The transformation was improved thanks to the screening of the reaction conditions and consequent improvements were obtained from the use of dicarbonylrhodium iodide [Rh(CO)2I]2 as catalyst precursor. The generalisation of the reaction was then further investigated by employing variously substituted arylboronic acids and propargylic alcohols.
- Dheur, Julien,Sauthier, Mathieu,Castanet, Yves,Mortreuxa, Andre
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experimental part
p. 557 - 561
(2010/06/13)
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- Direct C-H bond arylation of (Hetero)arenes with Aryl and heteroarylboronic acids
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A novel microwave-promoted protocol mediated by Mn(OAc)3 was developed for the single-electron-transfer oxidative direct C-H bond arylation of (hetero)arenes with aryl and hetero-arylboronic acids. Various electron-deactivated and electron-rich heteroarenes and benzene underwent successfully the direct arylation in this general process. The use of slight excess of heteroarene or benzene in this method was found to be sufficient. Georg Thieme Verlag Stuttgart New York.
- Guchhait, Sankar K.,Kashyap, Maneesh,Saraf, Shuddham
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experimental part
p. 1166 - 1170
(2010/06/11)
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- Synthesis of 2-aryl- and 2,5-diarylfurans and thiophenes by Suzuki-Miyaura reactions using potassium trifluoroborate salts and heteroaryltellurides
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The Suzuki-Miyaura cross-coupling reaction of 2-(butyltellanyl) or 2,5-bis-(butyltellanyl)furans and thiophenes with potassium aryltrifluoroborate salts catalyzed by palladium afforded 2-aryl- or 2,5-diaryl-furans and thiophenes in moderate to good yields.
- Botteselle, Giancarlo V.,Hough, Thomas L. S.,Venturoso, Raphael C.,Cella, Rodrigo,Vieira, Adriano S.,Stefani, Helio A.
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experimental part
p. 870 - 873
(2009/04/11)
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- A practical variation on the Paal-Knorr pyrrole synthesis
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The radical addition of α-xanthyl ketones to vinyl pivalate gives adducts that are synthetic equivalents of 1,4-ketoaldehydes; treatment with ammonia or primary amines leads to the corresponding pyrroles in high yield.
- Quiclet-Sire, Béatrice,Quintero, Leticia,Sanchez-Jimenez, Graciela,Zard, Samir Z.
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- SUBSTITUTED FURANS AS INHIBITORS OF 3-HYDROXY-3-METHYLGLUTARYL-COA REDUCTASE
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Compounds of the formula: STR1 in which STR2 where M is hydrogen or alkyl; one of R 2 and R 3 is phenyl or substituted phenyl where the substituent is alkyl, alkoxy, halogen, trifluoromethyl, nitro, amino, cyano or carboxyl; and the other
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