- Electrochemical fluorosulfonylation of styrenes
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An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.
- Jiang, Yi-Min,Wu, Shao-Fen,Yan, Hong,Ye, Ke-Yin,Yu, Yi,Yuan, Yaofeng
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supporting information
p. 11481 - 11484
(2021/11/16)
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- Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes
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Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.
- Jiang, Yimin,Shi, Zhaojiang,Wu, Jinnan,Wu, Shaofen,Ye, Keyin,Yu, Yi,Yuan, Yaofeng
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supporting information
(2021/11/17)
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- Synthesis method of p-acetoxystyrene
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The invention discloses a synthesis method of p-acetoxystyrene, which relates to the field of organic synthesis. The synthesis route of the synthesis method is as follows: 1, adding p-hydroxyacetophenone and an acetylation reagent into a first solvent, and carrying out esterification reaction under an alkaline condition to generate p-acetoxyacetophenone, 2, adding p-acetoxyacetophenone into a second solvent, and reducing the p-acetoxyacetophenone into 4-acetoxyphenyl methyl methanol under the catalysis of a catalyst in a hydrogen atmosphere, and 3, dehydrating the 4-acetoxyphenyl methyl methanol in an alkaline ionic liquid to obtain the p-acetoxystyrene. The method is high in yield, low in three wastes, green and clean, and the recovery cost and the equipment cost are reduced.
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Paragraph 0033; 0036; 0037-0044
(2021/04/26)
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- Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
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Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
- Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
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supporting information
p. 4097 - 4109
(2021/08/31)
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- Mild and efficient desulfurization of thiiranes with MoCl5/Zn system
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Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.
- Lee, Yeong Jin,Shin, Jeong Won,Yoo, Byung Woo
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- The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan
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The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.
- Chen, Miaomiao,Ding, Xin,Gao, Yongyue,He, Xingxing,Kang, Jin,Lu, Aidang,Wang, Qingmin,Wang, Ziwen,Zhang, Mingjun
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supporting information
p. 9140 - 9143
(2021/09/14)
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- Preparation method of p-acetoxystyrene
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The invention relates to the field of organic chemistry, and in particular, relates to a preparation method of p-acetoxystyrene. The preparation method of p-acetoxystyrene provided by the invention comprises the steps: carrying out a reaction of p-hydroxyacetophenone with an acetylation reagent to prepare p-acetoxyacetophenone; carrying out hydrogenation reduction on p-acetoxyacetophenone to prepare 1-(4-acetoxyphenyl)ethanol; and carrying out an elimination reaction on 1-(4-acetoxyphenyl)ethanol to prepare p-acetoxystyrene. According to the preparation method of p-acetoxystyrene, starting from the most basic raw materials, three steps of reactions are carried out, especially in the third step of alkene formation reaction, alkaline elimination is creatively adopted, the defects that in traditional acid catalysis alkene formation elimination reaction, double-bond acid catalysis sudden side reactions are likely to happen, the reaction is likely to be out of control, and consequently theyield is low are overcome, and generated double bonds can stably exist for a long time in a reaction system.
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Paragraph 0088-0093; 0099-0107
(2020/01/14)
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- Synthetic method of p-acetoxystyrene
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The invention relates to a synthetic method of p-acetoxystyrene, in particular to a novel process for synthesizing p-acetoxystyrene serving as an intermediate of 248-nm photoresist monomer p-hydroxystyrene. The method comprises the following steps of: performing solid acid catalysis on p-hydroxyphenethyl alcohol serving as a raw material, and performing dehydrating in an organic solvent in the presence of a polymerization inhibitor to obtain a target product. According to the synthetic method of p-acetoxystyrene, the p-hydroxyphenethyl alcohol is taken as the raw material for solid acid catalysis to prepare the 248-nm photoresist monomer p-hydroxystyrene intermediate p-acetoxystyrene through one-pot boiling, and the new synthesis process has the advantages that the yield is high, a catalyst is easy to recycle and reuse, few three wastes are generated and the like.
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Paragraph 0017-0022
(2020/05/29)
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- Copper-Catalyzed Asymmetric Radical 1,2-Carboalkynylation of Alkenes with Alkyl Halides and Terminal Alkynes
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A copper-catalyzed intermolecular three-component asymmetric radical 1,2-carboalkynylation of alkenes has been developed, providing straightforward access to diverse chiral alkynes from readily available alkyl halides and terminal alkynes. The utilization of a cinchona alkaloid-derived multidentate N,N,P-ligand is crucial for the efficient radical generation from mildly oxidative precursors by copper and the effective inhibition of the undesired Glaser coupling side reaction. The substrate scope is broad, covering (hetero)aryl-, alkynyl-, and aminocarbonyl-substituted alkenes, (hetero)aryl and alkyl as well as silyl alkynes, and tertiary to primary alkyl radical precursors with excellent functional group compatibility. Facile transformations of the obtained chiral alkynes have also been demonstrated, highlighting the excellent complementarity of this protocol to direct 1,2-dicarbofunctionalization reactions with C(sp2/sp3)-based reagents.
- Dong, Xiao-Yang,Cheng, Jiang-Tao,Zhang, Yu-Feng,Li, Zhong-Liang,Zhan, Tian-Ya,Chen, Ji-Jun,Wang, Fu-Li,Yang, Ning-Yuan,Ye, Liu,Gu, Qiang-Shuai,Liu, Xin-Yuan
-
supporting information
p. 9501 - 9509
(2020/05/18)
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- Selective and efficient desulfurization of thiiranes with Mo(CO)6
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Mo(CO)6 converts a broad range of thiiranes to the corresponding alkenes in high yields under neutral conditions. It has been found that this protocol is chemoselective and tolerates a variety of functional groups such as chloro, bromo, fluoro, ester, methoxy, ether and keto.
- Yoo, Byung Woo,Kim, Jung Youn
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- Synthesis method of pterostilbene
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The invention provides a synthesis method of pterostilbene. The synthesis method takes 4-hydroxybenzaldehyde as a raw material and comprises the following steps: carrying out acetylation reaction to generate 4-acetoxybenzaldehyde; then carrying out wittig reaction to generate 4-acetoxystyrene; carrying out hydrolysis reaction on 4-acetoxystyrene to generate 4-hydroxystyrene; carrying out Heck reaction on 4-hydroxystyrene to obtain a target product pterostilbene. The method provided by the invention has the advantages of easiness for obtaining the raw materials, high product selectivity, relatively high yield, moderate reaction conditions and simplicity in operation.
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Paragraph 0029; 0030; 0037; 0042
(2018/09/21)
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- METHOD FOR THE SYNTHESIS AND PRODUCTION OF ALKENYL COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing an efficient alkenyl compound conveniently and inexpensively. SOLUTION: A first compound represented by formula (1) reacts with a second compound represented by formula (3), in the presence of amino acid, in solvent containing amine, in a range of 50-200°C, to produce an alkenyl compound represented by formula (A) [where R1 is hydrogen or an optionally substituted C1-C30 alkyl group, R2 is a carboxyl group or the like, R3 and R4 are hydrogen, an optionally substituted C1-C30 alkyl group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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- Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base
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Transition-metal-free synthesis of β-alkoxy monohydroperoxides via aerobic photooxidation using an acridinium photocatalyst was developed. This method enables the synthesis of some novel hydroperoxides. The peroxide source is molecular oxygen, which is cost-effective and atomically efficient. Magnesium oxide plays an important role as a base in the catalytic system.
- Asano, Yuya,Nagasawa, Yoshitomo,Yamaguchi, Eiji,Itoh, Akichika
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supporting information
p. 409 - 412
(2018/02/21)
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- Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes
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The copper(II)-promoted free-radical oxidative difunctionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by 18O-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.
- Hussain, Muhammad Ijaz,Feng, Yangyang,Hu, Liangzhen,Deng, Qingfu,Zhang, Xiaohui,Xiong, Yan
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p. 7852 - 7859
(2018/05/30)
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- Environmental-friendly method for synthesizing acyloxy substituted styrene compound
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The invention relates to an environmental-friendly method for synthesizing an acyloxy substituted styrene compound. The method comprises the following steps of S1, at the temperature of being lower than or equal to 0 DEG C, performing reaction on the hydroxyl substituted styrene compounds, basic catalysts, a first part of polymerization inhibitors and acetylation reagents in organic solvents for afirst preset time period to obtain a first reaction mixture; S2, filtering the first reaction mixture; performing filtering to obtain a filter cake; adding lower alcohol and the second part of polymerization inhibitors into obtained filter liquid; performing reaction for a second preset time period to obtain a liquid mixture containing acyloxy substituted styrene compound; concentrating the liquid mixture; recovering the at least one part of organic solvents to obtain the acyloxy substituted styrene compound. The method provided by the invention has the advantages that organic solvents can bedirectly recovered; in addition, in the process of synthesizing the acyloxy substituted styrene compound, water is not used, so that waste water cannot be generated; the environment protection is facilitated.
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Paragraph 0044; 0045; 0048-0051
(2019/01/07)
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- Electronically Mismatched Cycloaddition Reactions via First-Row Transition Metal, Iron(III)-Polypyridyl Complex
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The iron(III)-polypyridyl complex and its derivatives showed sufficient oxidizing potential to act as a one-electron oxidant, producing radical cations from olefins and promoting the efficient radical cation [2 + 2] and [2 + 4] cycloaddition reactions. Subsequent chain propagation afforded trisubstituted cyclobutane or cyclohexene derivatives, and this facile route enables the replacement of rare metals with sustainable, green, and inexpensive iron in radical cation cycloadditions.
- Shin, Jung Ha,Seong, Eun Young,Mun, Hyeon Jin,Jang, Yu Jeong,Kang, Eun Joo
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supporting information
p. 5872 - 5876
(2018/09/25)
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- Rapid and efficient debromination of vic-dibromides with VCl3/indium system
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The VCl3/In system was found to be a new protocol for debromination of a variety of vic-dibromides to the corresponding alkenes in high yields with short reaction times under mild conditions. This new methodology is highly chemose-lective, tolerating several functional groups such as chloro, bromo, fluoro, keto, ester, carboxyl, and methoxy groups.
- Woo Yoo, Byung,Yeon Park, Jee,Jong Shin, Hyo
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p. 275 - 278
(2018/08/21)
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- Photoinduced, copper-catalyzed three components cyanofluoroalkylation of alkenes with fluoroalkyl iodides as fluoroalkylation reagents
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In the past few years, Ru and Ir catalyzed photoredox radical coupling reactions have been widely applied in organic synthesis. In contrast, the applications of Cu catalysts in photoredox organic transformations were limited. We here report the first example of photoinduced, Cu-catalyzed three component cyanofluoroalkylation of alkenes by directly using fluoroalkyl iodides as fluoroalkylation reagents.
- Guo, Quanping,Wang, Mengran,Wang, Yanfang,Xu, Zhaoqing,Wang, Rui
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supporting information
p. 12317 - 12320
(2017/11/20)
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- Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1: H,1′ H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner
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We report a transition metal-free dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene (1) under mild conditions, in which trimethylsilyl halide and 4,4′-bipyridine were generated as byproducts. The synthetic protocol for this dehalogenation reaction was effective for a wide scope of dibromo compounds as substrates while keeping the various functional groups intact. Furthermore, the reduction of vicinal dichloro alkanes and vicinal dibromo alkenes also proceeded in a salt-free manner to afford the corresponding alkenes and alkynes.
- Rej, Supriya,Pramanik, Suman,Tsurugi, Hayato,Mashima, Kazushi
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supporting information
p. 13157 - 13160
(2017/12/26)
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- Oxidative trifluoromethylation and fluoroolefination of unactivated olefins
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Fluorine-containing organic compounds are gaining increasing importance in medicinal chemistry. Described herein is a mild and efficient method for the radical addition of olefins with TMSCF3 and TMSCF2R (R = COOEt or CF3) to deliver various α-trifluoromethylated ketones and α-fluoroolefinated ketones.
- Wu, Ye-Bin,Lu, Guo-Ping,Yuan, Tao,Xu, Zhu-Bing,Wan, Li,Cai, Chun
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supporting information
p. 13668 - 13670
(2016/11/29)
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- Copper-catalyzed efficient dithiocyanation of styrenes: Synthesis of dithiocyanates
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A novel Cu-catalyzed intermolecular chemoselectivity dithiocyanation of styrenes with ammonium thiocyanate has been developed under mild conditions. This reaction exhibits a wide range of functional-group tolerance in styrenes to afford various dithiocyanates. The reaction mechanism was primarily investigated and a radical process was proposed.
- Lv, Yunhe,Pu, Weiya,Cui, Hao,He, Jialin,Zhang, Qinmei
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supporting information
p. 1223 - 1229
(2016/08/05)
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- METHOD OF PRODUCING HYDROXYSTYRENE DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a method of producing hydroxystyrene compounds and their derivatives, simply in a high yield, by using relatively inexpensive and easily removable agents and relatively mild conditions. SOLUTION: A method of producing hydroxystyrene compounds comprises decarboxylating a hydroxycinnamic acid compound in a solvent containing at least one solvent having an amide bond in the presence of water and/or hydroxy-containing compound. A method of producing hydroxystyrene derivatives comprises reacting the hydroxystyrene compound with an acylating agent and/or a carbonic esterification agent. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0070
(2016/12/16)
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- Characterization of a novel multifunctional resveratrol derivative for the treatment of atrial fibrillation
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Background and Purpose Atrial fibrillation (AF) is the most common cardiac arrhythmia and is associated with an increased risk for stroke, heart failure and cardiovascular-related mortality. Candidate targets for anti-AF drugs include a potassium channel Kv1.5, and the ionic currents I KACh and late INa, along with increased oxidative stress and activation of NFAT-mediated gene transcription. As pharmacological management of AF is currently suboptimal, we have designed and characterized a multifunctional small molecule, compound 1 (C1), to target these ion channels and pathways. Experimental Approach We made whole-cell patch-clamp recordings of recombinant ion channels, human atrial IKur, rat atrial I KACh, cellular recordings of contractility and calcium transient measurements in tsA201 cells, human atrial samples and rat myocytes. We also used a model of inducible AF in dogs. Key Results C1 inhibited human peak and late Kv1.5 currents, frequency-dependently, with IC50 of 0.36 and 0.11 μmol·L-1 respectively. C1 inhibited I KACh (IC50 of 1.9 μmol·L-1) and the Nav1.5 sodium channel current (IC50s of 3 and 1 μmol·L-1 for peak and late components respectively). C1 (1 μmol·L-1) significantly delayed contractile and calcium dysfunction in rat ventricular myocytes treated with 3 nmol·L -1 sea anemone toxin (ATX-II). C1 weakly inhibited the hERG channel and maintained antioxidant and NFAT-inhibitory properties comparable to the parent molecule, resveratrol. In a model of inducible AF in conscious dogs, C1 (1 mg·kg-1) reduced the average and total AF duration. Conclusion and Implications C1 behaved as a promising multifunctional small molecule targeting a number of key pathways involved in AF.
- Baczko, Istvan,Liknes, David,Yang, Wei,Hamming, Kevin C.,Searle, Gavin,Jaeger, Kristian,Husti, Zoltan,Juhasz, Viktor,Klausz, Gergely,Pap, Robert,Saghy, Laszlo,Varro, Andras,Dolinsky, Vernon,Wang, Shaohua,Rauniyar, Vivek,Hall, Dennis,Dyck, Jason R.B.,Light, Peter E.
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- RESVERATROL ANALOGS AND THERAPEUTIC USES THEREOF
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Resveratrol analogs and their use to inhibit Kv1.5 channels are provided. The resveratrol analogs are useful in the treatment of atrial arrhythmias, including atrial fibrillation (AF). Exemplary resveratrol analogs are compounds of general Formula (I):
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- Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
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4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
- Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
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p. 3674 - 3691
(2013/06/27)
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- Facile and efficient method for the debromination of vic-dibromides to alkenes with BiCL3/Ga system
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BiCl3/Ga was found to be a mild, efficient, and chemoselective system for the debromination of a series of functionally and structurally various vic-dibromides. A broad range of functional groups (ester, carboxy, aldehyde, methoxy, chloro, and ketone) was tolerated under the reaction conditions and only trans olefins were obtained in good yields. Copyright Taylor & Francis Group, LLC.
- Yoo, Byung Woo,Kim, Seo Hee,Park, Young Kwang
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experimental part
p. 1632 - 1636
(2012/05/05)
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- Mild and efficient debromination of vic-dibromides to alkenes with fecl36h2o/indium system
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The FeCl36H2O/indium system efficiently causes debromination of various dibromides to the corresponding alkenes in good to excellent yields under mild conditions.
- Woo Yoo, Byung,Woo Choi, Jin,Hye Yang, Min
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experimental part
p. 1488 - 1493
(2009/09/27)
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- METHODS FOR CONVERSION OF TYROSINE TO P-HYDROXYSTYRENE AND P-HYDROXYCINNAMIC ACID
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Three different reaction steps were combined to provide methods for preparing p-hydroxystyrene and p-hydroxycinnamic acid monomers from tyrosine. The three steps include reductive alkylation of tyrosine, followed by oxidation to the N-oxide, and thermal Cope elimination. During Cope elimination, either p-hydroxycinnamic acid or p-hydroxystyrene was produced depending on the absence or presence of base, respectively. Additionally, p-acetoxystyrene may be prepared by reacting the prepared p-hydroxystyrene either directly or after isolation with an acetylating agent.
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Page/Page column 8
(2008/12/06)
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- Processes for conversion of tyrosine to p-hydroxystyrene and p-acetoxystyrene
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Tyrosine was converted to p-hydroxystyrene in a two-step reaction without purification of individual intermediates. Conditions were determined for bromination of tyrosine in which reactive intermediates were formed. The mixture of these intermediates was used directly in a second step reaction to produce p-hydroxystyrene. The p-hydroxystyrene was further acetylated to produce p-acetoxystyrene in the second step reaction vessel.
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Page/Page column 8
(2008/06/13)
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- Method for preparing hydroxystyrenes and acetylated derivatives thereof
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A method is provided for the thermal decarboxylation of a phenolic substrate in the presence of a non-amine basic catalyst to produce a vinyl monomer. The product of the decarboxylation reaction may additionally be acetylated in the presence of an acetylating agent in the same reaction vessel.
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Page/Page column 8-9
(2008/06/13)
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- Process of heterocoupling by electrolytic microbattery, use of cobalt for implementing said coupling and composition for doing so
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This invention has as its object a process for preparation of vinyl aryl derivatives by an electrochemical path. This process is defined in that it consists in subjecting a composition that comprises a cobalt salt, an aromatic halide and a vinyl ester to the action of a metal that is at least as reducing as zinc. Application to organic synthesis.
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- Germination and growth inhibitors from wheat (Triticum aestivum L.) husks
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On the basis of our findings that the germination of intact wheat seeds (with husks) belonging to dormancy varieties was restrained as compared with that of the dehusked seeds (grains), the germination inhibitors in the husks were explored. The water-soluble extracts from the husks were separated by the aid of inhibition assay experiments, resulting in the characterization of 2-phenylethyl alcohol 1, 4-vinylphenol 2 and its 2-methoxy derivative 3, and dihydroactinidiolide 4, all of which showed clear inhibition of germination at 500 ppm in aqueous solution. The related compounds 1-phenylethyl alcohol 5 and tetrahydroactinidiolide 6 were as active as 1 and 4, while no noticeable difference in activity was detected among both enantiomers and the DL-form of compounds 4-6. Clear synergistic relations were observed between 4 and 1 and also 4 and 3. Since the present inhibitors have been isolated from various kinds of seed plants, they may be responsible for the general germination inhibition in the seed plants.
- Kato, Tadahiro,Saito, Naoko,Kashimura, Kaori,Shinohara, Mariko,Kurahashi, Takuma,Taniguchi, Kohji
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p. 6307 - 6312
(2007/10/03)
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- Method of producing styrene derivatives
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A method of producing styrene derivatives expressed the general formula (2) by reacting a benzaldehyde derivative expressed by the general formula (1) with dibromomethane under the existence of zinc metal as well as an active chloride for producing various types of oxystyrene which are polymerized monomers as a photoresist material used in a high density integrated circuit process from easily available materials which also can easily be handled: (wherein R indicates a an alkyl group, alkoxyalkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a 5 or 6-atom heterocylclic groups, or an alkylsilyl group); (wherein R indicates any of the same substituents as those described above.)
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- Method for preparing a salt of 4-hydroxystyrene and for preparing 4-tertiary-butoxycarbonyloxystyrene therefrom
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The present invention pertains to a method of forming a salt of 4-hydroxystyrene by reacting 4-acetoxystyrene with a suitable base in a suitable solvent system. Subsequently, or simultaneously, the salt of 4-hydroxystyrene can be reacted, preferably in situ, with di-tertiary-butyl-dicarbonate to form 4-tertiary-butoxycarbonyloxystyrene.
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- Method for preparing a salt of 4-hydroxystyrene and for preparing 4-tertiary-butoxycarbonyloxystyrene therefrom
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4-Acetoxystyrene is reacted with a base in a solvent to form a salt of 4-hydroxystyrene via saponification. Alternatively, 4-hydroxystyrene is reacted with a base to form a salt of 4-hydroxystyrene. In the latter case, the 4-hydroxystyrene is prepared by the transesterification of 4-acetoxystyrene. Subsequently or simultaneously, the salt of 4-hydroxystyrene is reacted, preferably in situ. with di-tertiary-butyl-dicarbonate to form 4-tertiary-butoxycarbonyloxystyrene.
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- Process for the preparation of substituted styrenes
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A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
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- Synthesis of Functionalized Styrenes via Palladium-Catalyzed Coupling of Aryl Bromides with Vinyl Tin Reagents
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Highly functionalized styrene derivatives have been synthesized in a single step by the palladium-catalyzed coupling of aryl bromides with tributylethenylstannane.Aryl bromides substituted with electron-withdrawing groups couple rapidly under the reaction conditions while bromides containing electron-donating substituents require further addition of catalyst for complete conversion. 1,4-Dibromobenzene can be coupled in a highly selective fashion with either 1 or 2 equiv of tin reagent to give 4-bromostyrene or diethenylbenzene, respectively.
- McKean, D. R.,Parrinello, G.,Renaldo, A. F.,Stille, J. K.
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p. 422 - 424
(2007/10/02)
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- The Wittig Synthesis of Alkenes under Gas-Liquid Phase-transfer
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Under gas-liquid phase-transfer catalysis conditions, an aldehyde passed in the gaseous state through a solid bed of potassium carbonate and a phosphonium salt, results in the formation of an alkene which is obtained in good yield by condensation and is free from triphenylphosphine oxide, which remains adsorbed on the bed.
- Angeletti, Enrico,Tundo, Pietro,Venturello, Paolo
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p. 269 - 271
(2007/10/02)
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