- Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization
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Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity of the crystalline monoarylated products relative to the liquid starting materials should be attributed predominantly to the low diffusion efficiency of the former in the reaction mixture, which results in a selective monoarylation. The present study sheds light on a novel approach using in situ phase transitions in solids to design selective organic transformations that are difficult to achieve via conventional solution-based synthesis.
- Seo, Tamae,Kubota, Koji,Ito, Hajime
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supporting information
p. 9884 - 9889
(2020/05/19)
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- Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[ b]thiophenes
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The trithiocarbonate anion (CS32-) was generated in situ from CS2 and KOH in dimethyl sulfoxide by a simple method and used as a novel synthetic equivalent of the S2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. Additionally, this system was employed for the metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes. These compounds were obtained from a cheap and readily available sulfur source in moderate to good yields, with good functional group tolerance.
- Paix?o, Douglas B.,Rampon, Daniel S.,Salles, Helena D.,Soares, Eduardo G. O.,Bilheri, Filipe N.,Schneider, Paulo H.
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supporting information
p. 12922 - 12934
(2020/11/26)
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- Copper Nanoparticles on Ordered Mesoporous Carbon Nitride Support: a Superior Catalyst for Homo- and Cross-Coupling of Terminal Alkynes under Base-Free Conditions
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A novel ordered mesoporous carbon nitride (OMCN) was synthesized as a functionalized support with 2,4,6-trichloro-1,3,5-triazine and benzidine as starting materials in the presence of SBA-15 as a template. Copper nanoparticles were then loaded on the C–N material to achieve a novel nanocomposite catalyst (Cu NPs-OMCN). The nanocomposite was utilized as a highly efficient catalyst for homo- and cross-coupling of terminal alkynes under base-free conditions in ethanol, and various symmetrical and unsymmetrical 1,3-diynes were obtained with good to excellent yields. Moreover, based on this reaction, a one-pot approach to synthesize 2,5-disubstituted thiophenes and furans from terminal alkynes were developed. Furthermore, the heterogeneous catalyst could be recovered and reused conveniently for several times with satisfactory yields.
- Xu, Hang,Wu, Liangying,Tian, Jing,Wang, Jun,Wang, Peng,Niu, Xiyu,Yao, Xiaoquan
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p. 6690 - 6696
(2019/11/02)
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- Liquid crystal compounds and their production and use (by machine translation)
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The invention discloses a type of heterocyclic discotic liquid crystal compounds, and a preparation method and an application thereof. A structural general formula of the heterocyclic discotic liquid crystal compounds is represented by the formula I. The compounds represented by the formula I are correct according to nuclear magnetic detection. Based on problems of few TN-type optical compensation film researches in current stage, few discotic liquid crystal material types, complicated synthesis process, and storage difficulty, the invention provides the series of heterocyclic discotic liquid crystal compounds with a novel microwave synthesis method. The type of compounds have the advantages of easy-to-obtain materials, simple preparation, and high total yield. The invention has important application value in the researches of development and application of optical compensation film materials.
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Paragraph 0053-0056
(2018/05/16)
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- Reversible light-directed self-organized 3D liquid crystalline photonic nanostructures doped with azobenzene-functionalized bent-shaped molecules
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Blue phases in self-assembled 3D periodic nanostructures endowed with sensitive photoresponsive capability were prepared by doping bent-core molecules with photochromic azobenzene moieties. The molecular configurations are found to be critical to the stab
- Wang, Meng,Hu, Wei,Wang, Ling,Guo, Duan-Yi,Lin, Tsung-Hsien,Zhang, Lanying,Yang, Huai
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supporting information
p. 7740 - 7744
(2018/08/04)
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- The effects of asymmetric bent-shaped compounds on the temperature range and electro-optical performances of liquid crystalline blue phases
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A series of asymmetric and symmetric bent-shaped molecules with branched terminals were synthesized and characterized. Their effects on inducing blue phase and electro-optical performances were compared and analyzed experimentally. It was found that the asymmetric and symmetric compounds almost have the same effect on inducing and stabilizing blue phase, but the electro-optical performance of mixtures doped with asymmetric compounds are much better than that of mixtures doped with symmetric compounds for they have a totally different dielectric anisotropy which can contribute to a larger Kerr constant.
- Wang, Xin,He, Wan-Li,Yang, Zhou,Wang, Dong,Cao, Hui,Zheng, Zhi-Gang,Liu, Zhen,Liu, Xiang
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p. 110750 - 110757
(2016/12/07)
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- Aryl(triethyl)silanes for Biaryl and Teraryl Synthesis by Copper(II)-Catalyzed Cross-Coupling Reaction
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Aryl(triethyl)silanes are found to undergo cross-coupling with iodoarenes in the presence of catalytic amounts of CuBr2and Ph-Davephos, as well as cesium fluoride as a stoichiometric base. Because the silicon reagents are readily accessible through catalytic C?H silylation of aromatic substrates, the net transformation allows coupling of aromatic hydrocarbons with iodoarenes via triethylsilylation.
- Komiyama, Takeshi,Minami, Yasunori,Hiyama, Tamejiro
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supporting information
p. 15787 - 15791
(2016/12/16)
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- Polymerizable mesogen compound having improved photoreactive efficiency and polymerizable liquid crystal compositions containing the same
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The present invention relates to a polymerizable mesogen compound having improved photo-reaction efficiency by introducing an alpha-thiomethyl acrylate group as a photo-reactive group, and to a polymerizable liquid crystal composition containing the same. The polymerizable mesogen compound of the present invention has improved photo-reaction efficiency at a relatively low energy state by introducing an alpha-thiomethyl acrylate group as a photo-reactive group, retains excellent solubility in a host liquid crystal due to an asymmetric structure thereof, and improves stability of the pretilt angle after photo-crosslinking, and thus can be useful as a polymerizable liquid crystal composition, particularly, a polymerizable liquid crystal composition for a polymer stabilization alignment type liquid crystal display.
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Paragraph 0094; 0096; 0097
(2016/12/26)
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- Thiophene-core estrogen receptor ligands having superagonist activity
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To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross-coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selectivity. Most of the bis(hydroxyphenyl)-thiophenes were ERβ selective, whereas the tris(hydroxyphenyl)-thiophenes were ERα selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11. Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.
- Min, Jian,Wang, Pengcheng,Srinivasan, Sathish,Nwachukwu, Jerome C.,Guo, Pu,Huang, Minjian,Carlson, Kathryn E.,Katzenellenbogen, John A.,Nettles, Kendall W.,Zhou, Hai-Bing
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p. 3346 - 3366
(2013/06/04)
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- REACTIVE MESOGEN COMPOUND, LIQUID CRYSTAL COMPOSITION INCLUDING THE SAME, METHOD OF MANUFACTURING A DISPLAY PANEL, AND DISPLAY PANEL
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A reactive mesogen compound, a liquid crystal composition including the reactive mesogen compound, a method of manufacturing a display panel, and a display panel are disclosed. The reactive mesogen compound may be activated by light having a wavelength be
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Paragraph 0058; 0059
(2013/08/28)
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- 17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES
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The invention relates to 17beta-hydroxysteroid dehydrogenase type 1 (17betaHSD1) inhibitors, the preparation thereof and the use thereof for the treatment and prophylaxis of hormone-related, especially estrogen-related or androgen-related, diseases.
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Page/Page column 26
(2011/04/14)
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- Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species
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In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.
- Snegaroff, Katia,L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Nguyen, Tan Tai,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
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experimental part
p. 10280 - 10290
(2010/04/24)
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- Design, synthesis, biological evaluation and pharmacokinetics of bis(hydroxyphenyl) substituted azoles, thiophenes, benzenes, and aza-benzenes as potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1)
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17β-Estradiol (E2), the most potent female sex hormone, stimulates the growth of mammary tumors and endometriosis via activation of the estrogen receptor α (ERα). 17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1), which is responsible for the catalytic r
- Bey, Emmanuel,Marchais-Oberwinkler, Sandrine,Werth, Ruth,Negri, Matthias,Al-Soud, Yaseen A.,Kruchten, Patricia,Oster, Alexander,Frotscher, Martin,Birk, Barbara,Hartmann, Rolf W.
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experimental part
p. 6725 - 6739
(2009/11/30)
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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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- Design, synthesis, and structure-activity relationship of novel thiophene derivatives for β-amyloid plaque imaging
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Novel 2,5-diphenylthiophene derivatives were synthesized and structure activity relationship with regard to Aβ plaque binding was studied. Binding affinities of these compounds were found to range from 3.9 to >1000 nM, depending on the substitution patter
- Chandra, Rajesh,Kung, Mei-Ping,Kung, Hank F.
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p. 1350 - 1352
(2007/10/03)
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- Syntheses and properties of donor - Acceptor-type 2,5-diarylthiophene and 2,5-diarylthiazole
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Equation presented. Syntheses of differently substituted 2,5-diarylthiophenes and 2,5-diarylthiazoles are carried out with the palladium-catalyzed C-H substitution reaction using AgF as an activator. Remarkably strong photoluminescence is observed in 2,5-
- Masui, Kentaro,Mori, Atsunori,Okano, Kunihiko,Takamura, Kenji,Kinoshita, Motoi,Ikeda, Tomiki
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p. 2011 - 2014
(2007/10/03)
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- Nematic 2,5-disubstituted thiophenes
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A large number of new liquid crystals incorporating the 2,5-disubstituted thiophene ring have been prepared and their mesomorphic behaviour studied in order to systematically investigate the correlation between the molecular structure and mesomorphism of thiophene derivatives with different shapes, polarisability and polarity. As a consequence of these investigations we have prepared a new class of liquid crystals incorporating a 2,5-disubstituted thiophene ring and a conjugated trans-carbon-carbon double bond in the terminal chain. These novel thiophene derivatives are the first liquid crystals incorporating a 2,5-disubstituted thiophene ring to exhibit a nematic phase at room temperature. This enables the flexoelectric coefficients of a bent-shaped molecule to be measured directly and at room temperature for the first time to the authors' knowledge. Many of these new thiophenes exhibit a high birefringence and a high nematic clearing point and are of potential use as components of nematic mixtures in LCDs.
- Campbell, Neil L.,Duffy, Warren L.,Thomas, Gareth I.,Wild, Janine H.,Kelly, Stephen M.,Bartle, Kevin,O'Neill, Mary,Minter, Vicky,Tuffin, Rachel P.
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p. 2706 - 2721
(2007/10/03)
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- 1,2-Dithiines and precursors, XVI: Synthesis, structure, and reactivity of non-anellated 1,2-dithiines
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Various monocyclic 1,2-dithiines 6a,b,d-t were prepared via (Z,Z)-1,4-difunctionalized butadienes (4-11,19,20). A twisted cyclic structure A is unequivocally proved rather than of the ringopened valence isomer B. The reactivity of these 1,2-dithiines is d
- Schroth, Werner,Dunger, Simona,Billig, Frank,Spitzner, Roland,Herzschuh, Rainer,Vogt, Almut,Jende, Thomas,Israel, Gunter,Barche, Jens,Stroehl, Dieter,Sieler, Joachim
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p. 12677 - 12698
(2007/10/03)
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- Synthesis and Characterization of Novel p-Terphenoquinone Analogues Involving a Central Dihydrothiophenediylidene Structure
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The title quinones, 2,5-bis(4-oxo-2,5-cyclohexadien-l-ylidene)-2,5-dihydrothiophene and its tetraalkyl derivatives, were synthesized via 2-(4-alkoxyphenyI)thiophene and 2,5-bis(4-alkoxyphenyl)thiophene conveniently prepared by using palladium(0)-catalyzed
- Takahashi, Kazuko,Suzuki, Tsuyoshi,Akiyama, Kimio,Ikegami, Yusaku,Fukazawa, Yosbimasa
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p. 4576 - 4583
(2007/10/02)
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- REGIOCHEMISTRY OF THERMAL EXTRUSION OF SULFUR FROM 2,6-DIARYL-1,4-DITHIINS YIELDING 2,5- AND 3,4-DIARYLTHIOPHENES
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The predominant formation of 2,5-diarylthiophenes over the 3,4-diaryl isomers by thermolyses of a series of 2,6-diaryl-1,4-dithiins supports that this sulfur extrusion reaction proceeds by the mechanism involving the valence isomerization to thiocarbonyl
- Nakayama, Juzo,Shimomura, Masahiro,Iwamoto, Michiko,Hoshino, Masamatsu
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p. 1907 - 1910
(2007/10/02)
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