- Electrooxidative 1,2-Bromoesterification of Alkenes with Acids and N-Bromosuccinimide
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A simple three-component 1,2-bromoesterification of alkenes with acids and N-bromosuccinimide under electrochemical oxidative conditions is described. This transformation enables the construction of β-bromoalkyl esters via oxidative C-Br/C-O difunctionalization, where a variety of alkenes, including styrenes and cycloolefins, were well tolerated to react efficiently with a wide range of acids, such as aromatic acids, aliphatic acids, and amino acids.
- Wan, Chao,Song, Ren-Jie,Li, Jin-Heng
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- (TRIMETHYLSILYLMETHYL)TRIBUTYLTIN: A CONVENIENT IN SITU PRECURSOR OF TRIMETHYLSILYLMETHYLLITHIUM
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The transmetalation reaction between (trimethylsilylmethyl)tributyltin and n-butyllithium proceeds in quantitative yield at 0 deg C in a mixture of tetrahydrofuran and hexane to afford trimethylsilylmethyllithium and tetrabutyltin.The methylenation of aldehydes and ketones utilizing this in situ procedure is demonstrated.
- Seitz, David E.,Zapata, Antonio
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- Semihydrogenation of phenylacetylene over nonprecious Ni-based catalysts supported on AlSBA-15
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A series of nonprecious monometallic Ni/AlSBA-15 and bimetallic Ni–M (M = Zn, Ga, Cu, or Fe)/AlSBA-15 catalysts were prepared using a urea precipitation method and applied to the semihydrogenation of phenylacetylene. The catalysts were characterized by various techniques, showing that the Ni particle size of catalyst can be tuned by adjusting the Al content, and NiZn and NiGa supported catalysts exhibited geometric and electronic effects that originated from the bimetallic alloy. Among all the catalysts studied, NiZn3/AlSBA-15, with a turnover frequency of 10.89 s?1 comparable to that of precious Pd-based catalysts, presented the highest selectivity to styrene (90.3%) at nearly 100% conversion of phenylacetylene in semibatch operation. This catalyst was further evaluated in a continuous fixed-bed reactor for semihydrogenation of a model C8 aromatic fraction of pyrolysis gasoline (a mixture of phenylacetylene, styrene, ethylbenzene and xylene), which aimed at assessing its practical application of recovering styrene from pyrolysis gasoline. The results showed that at complete conversion of phenylacetylene, the styrene concentration in the product was always kept at a stable level and higher than its initial concentration over 100 h of time on stream, demonstrating high selectivity and good stability of NiZn3/AlSBA-15. Finally, the application of NiZn3/AlSBA-15 was extended to other phenylacetylene derivatives.
- Yang, Lei,Yu, Shiyi,Peng, Chong,Fang, Xiangchen,Cheng, Zhenmin,Zhou, Zhiming
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- Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents
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A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)benzimidazole (1e), reacts with a variety of aldehydes and ketones in the presence of either NaHMDS (-55 °C to rt) or t-BuOK (rt, 1 h) in DMF to give the corresponding terminal alkenes in high yields. The byproducts are easily removed, and the reaction conditions are mild and practical.
- Ando, Kaori,Kobayashi, Takahisa,Uchida, Nariaki
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- Palladium-catalyzed proaromatic C(Alkenyl)-H olefination: Synthesis of densely functionalized 1,3-dienes
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An example of proaromatic C(alkenyl)-H olefination is reported. This protocol utilized a free carboxylic acid as a directing group for C(alkenyl)-H activation of 1,4-cyclohexadiene and coupled with various alkenes. Direct and sequential bisolefinations of proaromatic acids were achieved. The synthetic applicability has been exhibited by [4 + 2] cycloaddition and decarboxylative aromatization of the resulting proaromatic 1,3-dienes. Additionally, several kinetic studies also have been carried out to elucidate the reaction mechanism.
- Wang, Yu-Chun,Huang, Yen-Hsiang,Tsai, Hung-Chang,Sidick Basha,Chou, Chih-Ming
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- The application of non-cross-linked polystyrene-supported triphenylarsine in Stille coupling reactions
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NCPS-AsPh3 is a soluble polymer-supported triphenylarsine that performed equally well compared to free triphenylarsine as ligands in the Stille cross-coupling reaction of organic electrophiles and organostannanes, with the advantage that it can be conveniently and efficiently separated from the reaction by precipitation, and recycled for further use. The performance of this non-cross-linked polystyrene-supported arsine was found to be generally superior in Stille coupling reactions over the analogous polymer-supported phosphine, paralleling observations on the free ligands. Palladium-catalyzed modification of the polymer-supported arsine was possible through Pd-Ar/As-Ph exchange. Exploiting the ease of isolation of the polymer-supported reagent, the modified arsine is recycled for reuse in the Stille reaction and has led to a reduction in the yield of undesired scrambling products.
- Lau, Kelvin Chi Yin,Chiu, Pauline
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- Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone
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The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.
- Ando, Kaori,Oguchi, Mai,Kobayashi, Takahisa,Asano, Haruka,Uchida, Nariaki
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- Catalyst-Free Enantiospecific Olefination with In Situ Generated Organocerium Species
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Described is the in situ formation of triorganocerium reagents and their application in catalyst-free Zweifel olefinations. These unique cerium species were generated through novel exchange reactions of organohalides with n-Bu3Ce reagents. The adequate electronegativity of cerium allowed for compensating the disadvantages of both usually functional-group-sensitive organolithium species and less reactive organomagnesium reagents. Exchange reactions were performed on aryl and alkenyl bromides, enabling enantiospecific transformations of chiral boron pinacol esters. Finally, these new organocerium species were engaged in selective 1,2-additions onto enolisable and sterically hindered ketones.
- Music, Arif,Hoarau, Clément,Hilgert, Nicolas,Zischka, Florian,Didier, Dorian
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- Simple and efficient protocol for the synthesis of functionalized styrenes from 1,2-dibromoethane and arylboronic acids
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(Matrix presented) A simple and efficient protocol for the preparation of functionalized styrenes is disclosed that employs the palladium-catalyzed cross-coupling reaction of arylboronic acids with vinyl bromide, generated in situ from 1,2-dibromoethane. The reaction is carried out under mild reaction conditions. Compared with the cross-coupling reactions usually employed to obtain vinylarenes, this protocol is very simple, overcomes the inconvenience of using of ethylene under pressure, and uses air-stable and widely available arylboronic acids instead of vinyl organometallic reagents.
- Lando, Vanusa R.,Monteiro, Adriano L.
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- Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B
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A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.
- Chen, Jingyun,Chen, Shufang,Jiang, Jun,Lu, Qianqian,Shi, Liyang,Xu, Zekun,Yimei, Zhao
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supporting information
(2021/11/09)
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- Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
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A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.
- Huang, Xia,Jin, Jian,Lei, Chuanhu,Su, Mincong
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supporting information
(2022/01/15)
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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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- Water-hydrogen-supplying iridium catalytic alkyne semi-reduction selective synthesis method Process for trans-olefines
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The method comprises the following steps: DPPE, COD, a catalyst, water and alkyne are subjected to reduction reaction of alkyne in an organic solvent, and cis-olefin is generated by reaction under nitrogen protection. The ligand DPPE, the catalyst, the water and the alkyne are subjected to a reduction reaction of alkyne in an organic solvent, and a trans-olefin is generated by the reaction under nitrogen protection. The reactor for the reduction reaction is a sealed pressure-resistant reactor, the temperature of the reduction reaction is 100 - 130 °C, and the reduction reaction time is 20 - 48h. The amount of the catalyst used is 5 - 20% of the molar amount of alkyne, and the amount of water is 10 - 50 times of the molar amount of alkyne. The ligand is used in an amount 0.2 - 5 times the molar amount of catalyst. The catalyst system disclosed by the invention has extremely high chemical reaction and stereoselectivity, and cis or trans olefinic products can be synthesized at high yield. The catalytic system has strong universality on substrates, and alkynes containing various functional groups can efficiently carry out high-selectivity reduction reaction.
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Paragraph 0127-0130
(2021/09/29)
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- Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source
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The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is
- Shen, Guoli,Liu, Haojie,Chen, Jingchao,He, Zhenxiu,Zhou, Yongyun,Wang, Lin,Luo, Yang,Su, Zhimin,Fan, Baomin
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supporting information
p. 3601 - 3610
(2021/05/04)
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- Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration
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We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1,1-carboboration to be the C-C bond-forming step.
- Hasenbeck, Max,Wech, Felix,Averdunk, Arthur,Becker, Jonathan,Gellrich, Urs
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supporting information
p. 5518 - 5521
(2021/06/12)
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- Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides
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A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.
- Dong, Bingbing,Lu, Jiansha,Bao, Honghao,Zhang, Yuanyuan,Liu, Yingguo,Leng, Yuting
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supporting information
p. 3769 - 3776
(2021/07/14)
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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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- Base-Mediated Site-Selective Hydroamination of Alkenes
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We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.
- Koh, Ming Joo,Lee, Boon Chong,Li, Ping,Zhang, Xiaoxiang
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supporting information
(2021/12/29)
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- Polymerization of Allenes by Using an Iron(II) β-Diketiminate Pre-Catalyst to Generate High Mn Polymers
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Herein, we report an iron(II)-catalyzed polymerization of arylallenes. This reaction proceeds rapidly at room temperature in the presence of a hydride co-catalyst to generate polymers of weight up to Mn=189 000 Da. We have determined the polymer structure and chain length for a range of monomers through a combination of NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC) analysis. Mechanistically, we postulate that the co-catalyst does not react to form an iron(II) hydride in situ, but instead the chain growth is proceeding via a reactive Fe(III) species. We have also performed kinetic and isotopic experiments to further our understanding. The formation of a highly unusual 1,3-substituted cyclobutane side-product is also investigated.
- Durand, Derek J.,Webster, Ruth L.,Woof, Callum R.
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supporting information
p. 12335 - 12340
(2021/07/19)
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- Switchable Chemoselectivity of Reactive Intermediates Formation and Their Direct Use in A Flow Microreactor
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A chemoselectivity switchable microflow reaction was developed to generate reactive and unstable intermediates. The switchable chemoselectivity of this reaction enables a selection for one of two different intermediates, an aryllithium or a benzyl lithium, at will from the same starting material. Starting from bromo-substituted styrenes, the aryllithium intermediates were converted to the substituted styrenes, whereas the benzyl lithium intermediates were engaged in an anionic polymerization. These chemoselectivity-switchable reactions can be integrated to produce polymers that cannot be formed during typical polymerization reactions.
- Ashikari, Yosuke,Tamaki, Takashi,Kawaguchi, Tomoko,Furusawa, Mai,Yonekura, Yuya,Ishikawa, Susumu,Takahashi, Yusuke,Aizawa, Yoko,Nagaki, Aiichiro
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supporting information
p. 16107 - 16111
(2021/10/12)
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- Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
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The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.
- Juliá, Fabio,Paulus, Fritz,Ritter, Tobias,Yan, Jiyao
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supporting information
p. 12992 - 12998
(2021/09/03)
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- KO-t-Bu Catalyzed Thiolation of β-(Hetero)arylethyl Ethers via MeOH Elimination/hydrothiolation
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Herein, we describe a KO-t-Bu catalyzed thiolation of β-(hetero)arylethyl ethers through MeOH elimination to form (hetero)arylalkenes followed by anti-Markovnikov hydrothiolation to afford linear thioethers. The system works well with a variety of β-(hetero)arylethyl ethers, including electron-deficient, electron-neutral, electron-rich, and branched substrates and a range of aliphatic and aromatic thiols.
- Shigeno, Masanori,Shishido, Yoshiteru,Hayashi, Kazutoshi,Nozawa-Kumada, Kanako,Kondo, Yoshinori
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supporting information
p. 3932 - 3935
(2021/08/24)
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- Synthesis method of monosubstituted styrene
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The invention discloses a synthetic method of monosubstituted styrene. According to the method, monosubstituted benzaldehyde and methyltriphenylphosphonium bromide are used as initial raw materials, tetrahydrofuran is used as a solvent, strong base without nitrogen protection and low-temperature reaction conditions is used for reaction at normal temperature and normal pressure, and after the reaction is finished, a flash column chromatography method is used for post-treatment to obtain monosubstituted styrene. According to the method, water-free and oxygen-free harsh operation conditions are avoided, and the synthesis cost is reduced; the post-treatment process is simplified, quenching and extraction operations are not needed, the post-treatment time is shortened, a large amount of eluentdoes not need to be used, and the product loss is reduced.
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Paragraph 0038-0040; 0043-0044; 0055-0064; 0065-0068
(2020/05/05)
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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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- Method for preparing alkene compound from alkyne compound
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The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing an alkene compound from an alkyne compound. The method comprises the following step: reacting an alkyne compound in the presence of a photocatalyst and alkali under illumination to obtain an alkene compound. A sacrificial agent used in the invention can be used as a reaction solvent. The preparation method provided by the invention can inhibit the over-reduction of the alkyne compound to obtain an alkene compound. The method has the advantages of mild reaction conditions and simple operation, and can efficiently and greenly synthesize an alkene compound.
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Paragraph 0057-0058
(2020/07/03)
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- An Annelated Mesoionic Carbene (MIC) Based Ru(II) Catalyst for Chemo- And Stereoselective Semihydrogenation of Internal and Terminal Alkynes
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The catalytic utility of [RuL1(CO)2I2] (1), containing an annelated π-conjugated imidazo-naphthyridine-based mesoionic carbene (MIC) ligand (L1), is evaluated for E-selective alkyne semihydrogenation. The precatalyst 1, in combination with 2 equiv of AgBArF, semihydrogenates a broad range of internal alkynes with molecular hydrogen (5 bar) in water. (E)-Alkenes are accessed in high yields, and a number of reducible functional groups are tolerated. A chelate MIC ligand and two cis carbonyls provide a well-defined platform at the Ru center for hydrogenation and isomerization. The loss of two iodides and the presence of two carbonyls render the Ru center electron deficient and thus the formation of metal vinylidenes with terminal alkynes is avoided. This is leveraged for the semihydrogenation of terminal alkynes by the same catalytic system in isopropyl alcohol. Reaction profile, isomerization, kinetic, and DFT studies reveal initial alkyne hydrogenation to a (Z)-alkene, which further isomerizes to an (E)-alkene via metal-catalyzed Z → E isomerization.
- Bera, Jitendra K.,Choudhury, Joyanta,Das, Shubhajit,Dutta, Indranil,Pati, Swapan K.,Saha, Sayantani,Yadav, Suman
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p. 3212 - 3223
(2020/10/02)
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- Piperazine-promoted gold-catalyzed hydrogenation: The influence of capping ligands
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Gold nanoparticles (NPs) combined with Lewis bases, such as piperazine, were found to perform selective hydrogenation reactions via the heterolytic cleavage of H2. Since gold nanoparticles can be prepared by many different methodologies and using different capping ligands, in this study, we investigated the influence of capping ligands adsorbed on gold surfaces on the formation of the gold-ligand interface. Citrate (Citr), poly(vinyl alcohol) (PVA), polyvinylpyrrolidone (PVP), and oleylamine (Oley)-stabilized Au NPs were not activated by piperazine for the hydrogenation of alkynes, but the catalytic activity was greatly enhanced after removing the capping ligands from the gold surface by calcination at 400 °C and the subsequent adsorption of piperazine. Therefore, the capping ligand can limit the catalytic activity if not carefully removed, demonstrating the need of a cleaner surface for a ligand-metal cooperative effect in the activation of H2 for selective semihydrogenation of various alkynes under mild reaction conditions.
- Barbosa, Eduardo C. M.,Camargo, Pedro H. C.,Fiorio, Jhonatan L.,Hashmi, A. Stephen K.,Kikuchi, Danielle K.,Rossi, Liane M.,Rudolph, Matthias
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p. 1996 - 2003
(2020/04/22)
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- Creation of Redox-Active PdSx Nanoparticles Inside the Defect Pores of MOF UiO-66 with Unique Semihydrogenation Catalytic Properties
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Semihydrogenation of alkynes to produce alkenes is very important in the industry; however, over-hydrogenation heavily complicates the postprocesses, which are highly energy consuming and not environmentally friendly. One of the most efficient pathways to solve this challenging issue is to develop highly selective catalysts that could only hydrogenate alkynes and are inactive in hydrogenation of alkenes. This work presents herein an efficient catalyst, consisting of in situ created PdS0.53 nanoparticles as the redox-active sites inside the defect pores of metal–organic framework UiO-66, which demonstrates very high alkene selectivity (up to 99.5%) in semihydrogenation of easily over-hydrogenated terminal alkynes. In contrast to the traditional catalysts, strict control over the reaction time becomes the nonessential condition because the catalyst system is almost inactive in hydrogenation of alkenes. Therefore, this paradigm work provides a practically applicable pathway for the development of efficient catalysts with unique catalytic properties for selective semihydrogenation reactions.
- Dong, Ming-Jie,Wang, Xuan,Wu, Chuan-De
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- Fabrication of Ni3N nanorods anchored on N-doped carbon for selective semi-hydrogenation of alkynes
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Nickel is a highly active catalyst for the semi-hydrogenation of alkynes. However, the low selectivity of the alkene product caused by the over-hydrogenation reaction on Ni has hindered its practical applications. In this work, we report a new nickel nitride (Ni3N)-catalyzed semi-hydrogenation of alkynes to the corresponding alkenes. The Ni3N nanorods were facilely fabricated via a direct pyrolysis of the solid mixture of nickel acetate tetrahydrate and melamine (Mlm). The Ni3N phase in the optimum catalyst (Ni3N/NC-6/5-550) is shown to be effective and stable in the semi-hydrogenation of alkynes, with a high yield and good selectivity for alkenes (Z/E ratios up to >99/1). Both terminal and internal alkynes bearing a broad scope of functional groups are readily converted into alkenes with good chemo- and stereoselectivity. Notably, it was found that the over-hydrogenation can be markedly suppressed even at high conversion of alkyne. Density functional theory (DFT) calculations reveal that the low interaction between the alkene product and the Ni3N might plays a critical role in the selectivity enhancement.
- Shi, Xiaozhen,Wen, Xin,Nie, Shilin,Dong, Jie,Li, Jingde,Shi, Yongqing,Zhang, Huiling,Bai, Guoyi
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- Selective Transfer Semihydrogenation of Alkynes with H2O (D2O) as the H (D) Source over a Pd-P Cathode
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We reported a selective semihydrogenation (deuteration) of numerous terminal and internal alkynes using H2O (D2O) as the H (D) source over a Pd-P alloy cathode at a lower potential. P-doping caused the enhanced specific adsorption of alkynes and the promoted intrinsic activity for producing adsorbed atomic hydrogen (H*ads) from water electrolysis. The semihydrogenation of alkynes could be accomplished at a lower potential with up to 99 % selectivity and 78 % Faraday efficiency of alkene products, outperforming pure Pd and commercial Pd/C. This electrochemical semihydrogenation of alkynes might proceed via a H*ads addition pathway rather than a proton-coupled electron transfer process. The decreased amount of H*ads at a lower potential and the more preferential adsorption of the Pd-P to C≡C π bond than C=C moiety resulted in the excellent alkene selectivity. This method was capable of producing mono-, di-, and tri-deuterated alkenes with up to 99 % deuterium incorporation.
- Liu, Cuibo,Lu, Siyu,Wang, Changhong,Wu, Yongmeng,Zhang, Bin
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supporting information
p. 21170 - 21175
(2020/09/11)
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- Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus
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Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.
- Song, Di,Bi, Fangchao,Zhang, Nan,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Ma, Shutao
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supporting information
(2020/09/11)
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- Metal-free and base-free decarboxylation of substituted cinnamic acids in a deep eutectic solvent
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A metal-free and base-free strategy was developed in DES to synthesize styrenes for the first time by decarboxylation of cinnamic acid derivatives, which provided a renewable and cost efficiently protocol to access various styrenes including those with functional groups such as 4-vinylphenol and 1-chloro-4-vinylbenzene.
- Chen, Chen,Jian, Yuqing,Lei, Yuxin,Li, Bin,Peng, Caiyun,Sheng, Wen-Bing,Sumera, Yasmin,Wang, Wei,Zhang, Ming
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p. 558 - 563
(2020/01/24)
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- Efficient palladium-catalyzed synthesis of 2-aryl propionic acids
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A flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient sequential palladium-catalyzed Heck coupling of aryl bromides with ethylene and hydroxycarbonylation of the resulting styrenes to 2-aryl propionic acids. This cascade transformation leads with high regioselectivity to the desired products in good yields and avoids the need for additional purification steps.
- Neumann, Helfried,Sergeev, Alexey G.,Spannenberg, Anke,Beller, Matthias
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supporting information
(2020/09/16)
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- Deoxygenation of Epoxides with Carbon Monoxide
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The use of carbon monoxide as a direct reducing agent for the deoxygenation of terminal and internal epoxides to the respective olefins is presented. This reaction is homogeneously catalyzed by a carbonyl pincer-iridium(I) complex in combination with a Lewis acid co-catalyst to achieve a pre-activation of the epoxide substrate, as well as the elimination of CO2 from a γ-2-iridabutyrolactone intermediate. Especially terminal alkyl epoxides react smoothly and without significant isomerization to the internal olefins under CO atmosphere in benzene or toluene at 80–120 °C. Detailed investigations reveal a substrate-dependent change in the mechanism for the epoxide C?O bond activation between an oxidative addition under retention of the configuration and an SN2 reaction that leads to an inversion of the configuration.
- Maulbetsch, Theo,Jürgens, Eva,Kunz, Doris
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p. 10634 - 10640
(2020/07/30)
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- Transition Metal Free Nucleophilic Benzylation of Nitroarenes. Umpolung of the Friedel Crafts Reaction
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Benzyl chloride and its derivatives are efficiently deprotonated with strong bases to form α-chlorocarbanions. These anions are long-lived enough to enter VNS reactions with nitroarenes or nitroheteroarenes to give a variety of unsymmetrical o- and p-nitrodiarylmethanes. Selectivity of the reaction can be controlled to some extent by changing metal counterions of the base. (Figure presented.).
- Kisiel, Kacper,Brze?kiewicz, Jakub,Loska, Rafa?,M?kosza, Mieczys?aw
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p. 1641 - 1646
(2019/02/27)
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- Method for preparing styrene derivative from ionic liquid
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The invention belongs to the technical field of chemical engineering and pharmaceutical intermediate synthesis and relates to a method for preparing a styrene derivative from ionic liquid. The methodhas advantages that by adoption of the ionic liquid as a solvent, high reaction catalyzing efficiency is achieved; due to reusability of the ionic liquid, industrial production cost is saved, and theenvironment problem caused by traditional solvents can be solved helpfully.
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Paragraph 0026-0028
(2019/04/06)
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- Substituted styrene preparation method
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The invention belongs to the technical field of synthesis of chemical and medical intermediates, and relates to a substituted styrene preparation method, in particular to a method for preparing substituted styrene by using an ionic solution. In the method, the ionic solution is used as a solvent, and the reaction catalyzing efficiency is high. The ionic solution can be repeatedly used, industrialproduction cost is saved, and environment problems caused by a traditional solvent are solved favorably.
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Paragraph 0026-0028
(2019/02/26)
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- A method for the preparation of substituted styrene ion solution method
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The invention belongs to chemical and pharmaceutical intermediate synthesis technology field, relates to a process for preparing a substituted styrene ion solution method. The method takes the ionic liquid as solvent, reaction of high catalytic efficiency. The ionic liquid can be used repeatedly, save the industrialized production cost, and to facilitate the solution of the environmental problem of traditional solvent.
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Paragraph 0026; 0027; 0028
(2019/04/02)
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- Chemoenzymatic cascade for stilbene production from cinnamic acid catalyzed by ferulic acid decarboxylase and an artificial metathease
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We report the preparation of symmetrical stilbene derivatives in a two-step one-pot cascade reaction based on enzymatic decarboxylation of cinnamic acid followed by olefin cross metathesis. Embedment of the metathesis catalyst in a protein scaffold enabled the cascade reaction to symmetric stilbenes and furthermore very efficient removal of metal impurities (1 ppm in product fraction).
- Mertens, M. A. Stephanie,Sauer, Daniel F.,Markel, Ulrich,Schiffels, Johannes,Okuda, Jun,Schwaneberg, Ulrich
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p. 5572 - 5576
(2019/10/28)
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- Bimetallic Co/Al nanoparticles in an ionic liquid: Synthesis and application in alkyne hydrogenation
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Herein, we report the microwave-induced decomposition of various organometallic cobalt and aluminum precursors in an ionic liquid (IL), 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIm]NTf2), resulting in Co/Al nanoalloys with different molar Co/Al ratios. The dual-source precursor system of dicobalt octacarbonyl (Co2(CO)8) and pentamethylcyclopentadienyl aluminum ([AlCp?]4) in [BMIm]NTf2 afforded CoAl nanoparticles (CoAl-NPs) with a molar Co/Al ratio of 1?:?1. Their size and size distribution were determined via transmission electron microscopy (TEM) to be an average diameter of 3.0 ± 0.5 nm. Furthermore, the dual-source precursor system of cobalt amidinate ([Co(iPr2-MeAMD)2]) and aluminum amidinate [Me2Al(iPr2-MeAMD)] in molar ratios of 1?:?1 and 3?:?1 resulted in CoAl-and Co3Al-NPs with an average diameter of 3 ± 1 and 2.0 ± 0.2 nm, respectively. All the obtained materials were characterized via TEM, energy dispersive X-ray spectroscopy (EDX), selected area electron diffraction (SAED), together with high-angle annular dark-field scanning transmission electron microscopy (HAADF-STEM) and (high-resolution) X-ray photoelectron spectroscopy ((HR-)XPS). Phase-pure Co/Al-NPs were not obtained since the concomitant formation of Co-NPs and Al2O3 occurred in this wet-chemical synthesis. The as-prepared Co/Al nanoalloys were evaluated as catalysts in the hydrogenation of phenylacetylene under mild conditions (2 bar H2, 30 °C in THF). In comparison to the monometallic Co-NPs, the Co/Al-NPs showed a significantly higher catalytic hydrogenation activity. The Co-and Co/Al-NPs were also active under harsher reaction conditions (80 bar H2, 80 °C) without the addition of the activating co-catalyst DIBAL-H.
- Schmolke, Laura,Gregori, Bernhard J.,Giesen, Beatriz,Schmitz, Alexa,Barthel, Juri,Staiger, Lena,Fischer, Roland A.,Jacobi Von Wangelin, Axel,Janiak, Christoph
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p. 16583 - 16594
(2019/11/11)
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- Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes
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A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.
- Yang., Jinfei,Wang, Chengniu,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
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supporting information
p. 1903 - 1906
(2019/05/02)
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- Method for selective synthesis of cis-olefins and trans-olefins by semi-reduction of alcohol hydrogen supply palladium-catalyzed alkynes
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The invention provides a method for selective synthesis of cis-olefins and trans-olefins by semi-reduction of alcohol hydrogen supply palladium-catalyzed alkynes. The method comprises the following steps: performing alkyne reduction reaction with TEOA, NaOAc, a catalyst, alcohol and alkynes in an organic solvent and generating the cis-olefins after reaction; performing alkyne reduction reaction with a ligand, a catalyst, alcohol and alkynes in an organic solvent and generating the trans-olefins after reaction; a reactor for the reduction reaction is a sealed pressure-resistant reactor, the reduction reaction temperature is 120-150 DEG C, and the reduction reaction time is 20-48 hours; the dosage of the catalyst is 5-20 percent of the molar dosage of the alkynes, and the dosage of the alcohol is 10-100 times of the molar dosage of the alkynes; the dosage of R, R-DIPAMP is 0.5-5 times of the molar dosage of the alkynes. According to the method provided by the invention, a catalyst systemhas extremely-high chemical reaction and stereo-selectivity and can synthesize cis-olefin products or trans-olefin products with high yield; the catalyst system is good universality to a substrate, and the alkynes containing various functional groups can be efficiently subjected to the highly-selective reduction reactions.
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Paragraph 0196-0198
(2019/06/07)
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- Xanthate-mediated synthesis of (E)-alkenes by semi-hydrogenation of alkynes using water as the hydrogen donor
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Semi-hydrogenation of alkynes is one of the most widely used methods for obtaining alkenes in laboratory preparation and in industry. Transition metal catalysts have been extensively studied for this transformation, but the tolerance of functional groups, such as pyridine,-OH,-NH2,-Bpin, and halides, and the toxicity of the trace amount of transition metal catalysts are still highly challenging. In this study, we report a general and robust strategy to achieve the semi-hydrogenation of alkynes using inexpensive and commercially available xanthate as the mediator. Mechanism studies support a non-radical process and H2O acts as the hydrogen donor.
- Luo, Xianglin,Chen, Xiuwen,Chen, Lu,Zhang, Kun,Li, Yibiao
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supporting information
p. 2170 - 2173
(2019/02/24)
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- Control of Homocoupling Versus Reduction in Titanium(III)-Mediated Radical Opening of Styrene Oxides
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We describe the use of titanocene monochloride in the implementation of an experimental procedure that enables control of the homolytic opening of styrene oxides in a chemoselectively controlled manner. This leads either to homocoupling products or to phenethyl alcohol derivatives. The process occurs via the generation of benzyl radicals, which may undergo a) recombination or b) reduction, yielding benzyl-Ti(IV) species upon subsequent addition of H2O to the corresponding hydroxylated compounds. The main goal of this work is the study of the reactivity pattern of styrene oxides towards the formation of the mentioned products, thereby adding value to this interesting building block.
- González-Delgado, José A.,Arteaga, Jesús F.
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p. 7864 - 7869
(2019/12/27)
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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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- Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases
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Fungal ferulic acid decarboxylases (FDCs) belong to the UbiD-family of enzymes and catalyse the reversible (de)carboxylation of cinnamic acid derivatives through the use of a prenylated flavin cofactor. The latter is synthesised by the flavin prenyltransferase UbiX. Herein, we demonstrate the applicability of FDC/UbiX expressing cells for both isolated enzyme and whole-cell biocatalysis. FDCs exhibit high activity with total turnover numbers (TTN) of up to 55000 and turnover frequency (TOF) of up to 370 min?1. Co-solvent compatibility studies revealed FDC's tolerance to some organic solvents up 20 % v/v. Using the in-vitro (de)carboxylase activity of holo-FDC as well as whole-cell biocatalysts, we performed a substrate profiling study of three FDCs, providing insights into structural determinants of activity. FDCs display broad substrate tolerance towards a wide range of acrylic acid derivatives bearing (hetero)cyclic or olefinic substituents at C3 affording conversions of up to >99 %. The synthetic utility of FDCs was demonstrated by a preparative-scale decarboxylation.
- Aleku, Godwin A.,Prause, Christoph,Bradshaw-Allen, Ruth T.,Plasch, Katharina,Glueck, Silvia M.,Bailey, Samuel S.,Payne, Karl A. P.,Parker, David A.,Faber, Kurt,Leys, David
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p. 3736 - 3745
(2018/08/03)
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- Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: Hydrosilylation: versus semihydrogenation
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We herein report supported Pd nanoparticles on N,O-doped hierarchical porous carbon as a single operation catalyst-enabled additive-modulated reaction pathway for alkynes addition with organosilanes between hydrosilyation and semihydrogenation. In the case of alkynes hydrosilylation, a simple iodide ion as an additive has a promotion effect on the activity and regio- and stereoselectivity, where iodide can coordinate with Pd NPs via strong δ donation to increase the electron density of the Pd atom, resulting in an increased ability for the oxidative addition of hydrosilane as the rate-determining step to make the reaction proceed efficiently to afford vinylsilanes in high yields with excellent regio- and stereoselectivity. For the catalytic transfer semihydrogenation of alkynes, water was introduced to mix with organosilane to form a silanol together with the generation of hydrogen atoms on the Pd NPs surface or the liberation of H2 gas as a reducing agent, whereby the quantitative reduction of alkynes was achieved with exclusive selectivity to alkenes. In both cases, the catalyst could be recycled several times without a significant loss in activity or selectivity. A broad range of alkyl and aryl alkynes with various functional groups are compatible with the reaction conditions. The role the additive exerted in each reaction was extensively investigated through control experiments as well as the kinetic isotopic effect along with spectroscopic characterization. In addition, the respective mechanism operating in both reactions was proposed.
- Duan, Yanan,Ji, Guijie,Zhang, Shaochun,Chen, Xiufang,Yang, Yong
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p. 1039 - 1050
(2018/03/05)
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- Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: Synthesis of vicinal-dichlorides and chlorodienes
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Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benz-iodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved.
- Zhao, Zhensheng,Murphy, Graham K.
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supporting information
p. 796 - 802
(2018/04/16)
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- Rapid Access to Ortho-Alkylated Vinylarenes from Aromatic Acids by Dearomatization and Tandem Decarboxylative C-H Olefination/Rearomatization
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A two-step straightforward method for the preparation of ortho-alkylated vinylarenes from readily available benzoic acids is described. The synthetic route involves the dearomatization of benzoic acids by Birch reduction providing alkylated cyclohexa-2,5-dienyl-1-carboxylic acids. The diene subsequently undergoes a decarboxylative C-H olefination followed by rearomatization to deliver ortho-alkylated vinylarene. Mechanistic studies suggest that a Pd/Ag bimetallic catalytic system is important in the tandem decarboxylative C-H olefination/rearomatization step.
- Tsai, Hung-Chang,Huang, Yen-Hsiang,Chou, Chih-Ming
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supporting information
p. 1328 - 1332
(2018/03/09)
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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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- Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
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Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model-aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. (Figure presented.).
- Barlow, Helen,Buser, Jonas Y.,Glauninger, Hendrik,Luciani, Carla V.,Martinelli, Joseph R.,Oram, Niall,Thompson-Van Hook, Nichole,Richardson, Jeffery
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p. 2678 - 2690
(2018/06/04)
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- Terminal alkyne insertion into a thiolate-bridged dirhodium hydride complex derived from heterolytic cleavage of H2
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Thiolate-bridged dirhodium and diiridium complexes can facilely realize heterolytic cleavage of H2 across the metal-sulfur bond to generate the corresponding hydride bridged complexes. Furthermore, terminal alkynes can insert the Rh-H-Rh fragment to afford σ:π alkenyl bridged complexes and then convert to the corresponding alkenes in the presence of a reductant and an acid.
- Zhao, Xiangyu,Yang, Dawei,Zhang, Yahui,Wang, Baomin,Qu, Jingping
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supporting information
p. 11112 - 11115
(2018/10/15)
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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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- Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols
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Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diarylethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2] as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM][X] (X?=?PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2 with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)2 to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM][X] solvent is recycled and reused.
- Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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p. 150 - 161
(2017/06/30)
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