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Relevant bibliographies by topics / Acetylide coupling reaction

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Academic literature on the topic 'Acetylide coupling reaction'

Author: Grafiati

Published: 6 September 2023

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Journal articles on the topic "Acetylide coupling reaction"

1

Konno, Tsutomu, Gen Egashira, Chihiro Kajimoto, Takuto Kataoka, and Shigeyuki Yamada. "Synthesis and Application of Tetrafluoroethylene (CF2CF2)-Containing Acetylene Derivatives." Synthesis 52, no. 13 (March 5, 2020): 1947–58. http://dx.doi.org/10.1055/s-0039-1691744.

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On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl2·TMEDA complex, in the presence of Pd(PPh3)4 to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoroethylene group.

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2

Wu, Li, Li-fen Peng, Zhi-fang Hu, Hong Wang, Zi-long Tang, Yin-chun Jiao, and Xin-hua Xu. "Synthesis of cyclic phenyl hexayne from Me3Si-/Ph2P(O)-protected ethynes." Journal of Chemical Research 43, no. 11-12 (September 12, 2019): 503–6. http://dx.doi.org/10.1177/1747519819874419.

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A practical approach for the synthesis of cyclic phenyl hexayne is demonstrated through a one-pot deprotection/transformation of magnesium acetylide into a copper acetylide/Sonogashira coupling procedure, followed by dephosphination, Hay coupling, desilylation, and Eglinton coupling. This approach avoids tedious synthetic routes and harsh reaction conditions and affords the product in 41% yield.

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Cabezas, Jorge, Rebeca Poveda, and José Brenes. "One-Pot Conversion of Aldehydes and Ketones into 1-Substituted and 1,4-Disubstituted 1,3-Enynes." Synthesis 50, no. 17 (July 23, 2018): 3307–21. http://dx.doi.org/10.1055/s-0037-1610197.

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Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generates the operational equivalent of 1,3-dilithiopropyne, which upon treatment with aldehydes or ketones, produces the corresponding alkoxy lithium acetylide intermediates. Reaction of this alkoxide with tosyl chloride, and t-BuLi produces 1-substituted, or 1,1-disubstituted 1,3-enynes in a one-pot reaction. When this lithium acetylide intermediates, obtained by this procedure, were used to perform palladium-catalyzed cross-coupling reactions, followed by addition of thionyl chloride and pyridine, 1,4-disubstituted or 1,1,4-trisubstituted 1,3-enynes were obtained in a one-pot protocol.

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Andreica, Adriana Maria, Lucia Gansca, Irina Ciotlaus, and Ioan Oprean. "Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone." Revista de Chimie 68, no. 1 (February 15, 2017): 180–85. http://dx.doi.org/10.37358/rc.17.1.5415.

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Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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Andreica, Adriana-Maria, Lucia Gansca, Irina Ciotlaus, and Ioan Oprean. "A New Synthesis of the Sex Pheromone of the Indian Meal Moth Plodia Interpunctella hb. (Lepidoptera, Pyralidae)." Revista de Chimie 71, no. 1 (February 7, 2020): 201–5. http://dx.doi.org/10.37358/rc.20.1.7832.

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New synthesis of (9Z,12E)-9,12-tetradecadien-1-yl acetate, the sex pheromone of the indian meal moth Plodia interpunctella (Lepidoptera, Pyralidae), were developed. The synthesis was based on a C8+C2=C10 and C10+C4=C14 coupling scheme. The route involves, as the key step, the use of the mercury derivative of the terminal-alkyne -functionalised as intermediate.The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury.In the second coupling reaction, the mercury derivative was directly lithiated and then alkylated with (E)-1-bromo-2-butene obtaining 1-tert-butoxy-(9-yne,12E)-9,12-tetradecaenyne. After stereoselective reduction in the presence of NiP-2 catalyst and acetylation gave (9Z,12E)-9,12-tetradecadien-1-yl acetate with 82% isomeric purity.

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Yi, Chae S., and Nianhong Liu. "The Ruthenium Acetylide Catalyzed Cross-Coupling Reaction of Terminal and Internal Alkynes: Isolation of a Catalytically Active β-Agostic Intermediate Species." Organometallics 17, no. 15 (July 1998): 3158–60. http://dx.doi.org/10.1021/om980405g.

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YI, C. S., and N. LIU. "ChemInform Abstract: The Ruthenium Acetylide Catalyzed Cross-Coupling Reaction of Terminal and Internal Alkynes: Isolation of a Catalytically Active β-Agostic Intermediate Species." ChemInform 29, no. 46 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199846071.

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Deng, Danfeng, Dayun Huang, Xiangyu Sun, and Biwen Gao. "Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification." Synthesis 53, no. 19 (April 19, 2021): 3522–34. http://dx.doi.org/10.1055/a-1486-2158.

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AbstractRecent advances on the tandem difunctionalization of alkynes in the last decade (2010–2020) are summarized into five categories based on the type of mechanism: (1) radical addition and coupling for the synthesis of polysubstituted ketones and alkenes, (2) electrophilic addition of alkynes, (3) reactions mediated by haloalkynes or copper acetylides, (4) the preparation of cyclic compounds via radical processes, palladium-catalyzed reactions or conjugate additions, and (5) cyclic compounds as intermediates in ring openings. Herein, radical, electrophilic and nucleophilic reactions are discussed in detail. We hope this review will help to promote future research in this area. 1 Introduction2 Radical Addition and Coupling3 Electrophilic Addition4 Reactions Mediated by Haloalkynes or Copper Acetylides5 Cyclization6 Cyclization and Ring Opening7 Conclusions

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Koridze, A. A., V. I. Zdanovich, O. A. Kizas, A. I. Yanovsky, and Yu T. Struchkov. "Coupling and annelation of two acetylide groups and alkyne molecules in the reaction of (OC)5ReCCPh with ferrocenylacetylene. Crystal and molecular structure of Re2(CO)7{C8H2Ph2(C5H4FeC5H5)2} · acetone." Journal of Organometallic Chemistry 464, no. 2 (January 1994): 197–201. http://dx.doi.org/10.1016/0022-328x(94)87274-0.

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Aridi, Toufic, and Mario Gauthier. "Synthesis of Arborescent Polymers by “Click” Grafting." MRS Proceedings 1613 (2014): 23–31. http://dx.doi.org/10.1557/opl.2014.154.

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ABSTRACTA novel method was developed for the preparation of arborescent (dendritic graft) polymers, by successive grafting reactions of linear chain segments using alkyne-azide “click” chemistry coupling. A linear polystyrene substrate was thus randomly functionalized with acetylene functionalities, by acetylation and further reaction with propargyl bromide in the presence of potassium hydroxide and 18-crown-6 in toluene. The anionic polymerization of styrene was achieved with 6-tert-butyldimethylsiloxy-hexyllithium to obtain polystyrene with a protected hydroxyl chain end. Deprotection of the hydroxyl group, followed by conversion into tosyl and azide functionalities yielded the material serving as side chains in the grafting reactions. Coupling of the azide-terminated side chains with the acetylene-functionalized substrate in the presence of a Cu(I) catalyst proceeded in up to 93% yield. Additional cycles of substrate functionalization and side chain coupling led to arborescent polymers of generations G1 and G2, with low polydispersity indices (Mw/Mn≈ 1.1), in 60-84% yield. These polymers are characterized by a very compact structure, and molecular weights increasing geometrically over successive generations. A similar methodology was also shown to work for the synthesis of arborescent polybutadiene systems, using azide-functionalized substrates and alkyne-terminated side chains. The coupling reaction proceeded in up to 76% yield under optimized conditions for these systems.

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Dissertations / Theses on the topic "Acetylide coupling reaction"

1

Chii-Feng, Chiou, and 邱啟峰. "Nickle Complexed-Catalyzed the Coupling Reaction of Terminal Acetylene and aryl iodide with 7-Het- eroatom Norbornadiene." Thesis, 1995. http://ndltd.ncl.edu.tw/handle/09888695483900275677.

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Book chapters on the topic "Acetylide coupling reaction"

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Silva, Tiago J., Paulo J. Mendes, António P. S. Teixeira, M. Paula Robalo, and M. H. Garcia. "7.4. Sonogashira Coupling Reaction of Aryl Derivatives: A Versatile Method for Acetylide Building Blocks." In Comprehensive Organic Chemistry Experiments for the Laboratory Classroom, 564–67. The Royal Society of Chemistry, 2016. http://dx.doi.org/10.1039/9781849739634-00564.

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Kauffman, M. C., and P. J. Walsh. "Rhodium-Catalyzed Coupling of Acetylene." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00243.

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Carpentier, J. F., and E. Kirillov. "Poly(acetylene)." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00627.

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Hirsch, A., and O. Vostrowsky. "Convergent Synthesis of Polyynes by Acetylene Coupling Reactions." In Polyynes, Arynes, Enynes, and Alkynes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-043-00046.

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Hirsch, A., and O. Vostrowsky. "Iterative Synthesis of Polyynes Using Acetylene Coupling Reactions." In Polyynes, Arynes, Enynes, and Alkynes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-043-00053.

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Carpentier, J. F., and E. Kirillov. "Substituted Poly(acetylene)s." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00628.

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Aubert, C., M. Malacria, and C. Ollivier. "Bimolecular Cocyclization of Diynes and Acetylene." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00139.

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Aubert, C., M. Malacria, and C. Ollivier. "Carbocyclization of Acetylene and Aryl-Substituted Monoynes Bearing Phosphoryl Moieties." In Stereoselective Pericyclic Reactions, Cross Coupling, and C—H and C—X Activation, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-203-00099.

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Conference papers on the topic "Acetylide coupling reaction"

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Ezekoye, O. A., and Z. Zhang. "Radiation Simulation of a Microgravity Diffusion Flame." In ASME 1996 International Mechanical Engineering Congress and Exposition. American Society of Mechanical Engineers, 1996. http://dx.doi.org/10.1115/imece1996-0187.

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Abstract This study numerically investigates the effects of radiation from both the soot and gas phase species on the soot kinetics in a quasi-steady state microgravity spherical acetylene-air diffusion flame by coupling the soot and gas phase chemistry with radiative heat transfer processes. The gas phase reaction is modeled by two step chemical kinetics. The soot reaction mechanism includes nucleation, surface growth, oxidation and coagulation steps. The radiation from both soot and the gas phase are calculated by employing a spherical harmonics (P-1 approximation) model. The local Planck mean absorption coefficients of the computed species are specified in the computations. Unlike normal gravity acetylene-air steady state jet diffusion flames in which the radiation from soot dominates gas radiation effects, it is found that for a microgravity diffusion flame, except at very early times, the radiation from the gas products dominates soot radiation. In the microgravity flame configuration, it is noted that the radiation heat loss fraction (defined as the ratio of the radiation heat loss rate to the chemical heat release rate) increases up to 80% shortly after ignition.

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El-Asrag, H., and S. Menon. "Subgrid Modeling of Soot Formation in Non-Premixed Turbulent Flames." In ASME Turbo Expo 2007: Power for Land, Sea, and Air. ASMEDC, 2007. http://dx.doi.org/10.1115/gt2007-27593.

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A subgrid model for soot dynamics is developed for large-eddy simulation (LES) using the Method of Moment with Interpolative Closure (MOMIC). The soot model is implemented within a subgrid mixing and combustion model so that reaction-diffusion-MOMIC coupling is possible without requiring ad hoc filtering. The combined model includes the entire process, from the initial phase, when the soot nucleus diameter is much smaller than the mean free path, to the final phase, after coagulation and aggregation, where it can be considered in the continuum regime. The soot diffusion and the effect of the thermophoretic forces are included in the model. A relatively detailed but reduced kinetics for ethylene-air is used to simulate an experimentally studied non-premixed ethylene/air jet diffusion flame. In this formulation, acetylene is used as a soot precursor species. The soot volume fraction order of magnitude, the location of its maxima, and the soot particle size distribution are all captured reasonably. Along the centerline, an initial region dominated by nucleation and surface growth is established followed by an oxidation region. A possible initial log-normal distribution followed by a more gaussian distribution downstream the centerline is observed. Limitations of the current approach and possible solution strategies are also discussed.

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