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Добірка наукової літератури з теми "Aryne Chemistry"

Автор: Grafiati

Опубліковано: 6 вересня 2023

Оновлено: 19 квітня 2025

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Статті в журналах з теми "Aryne Chemistry"

Brown, Roger F. C. "Flash Vacuum Pyrolytic Generation of Arynes - in Retrospect." Australian Journal of Chemistry 63, no. 7 (2010): 1002. http://dx.doi.org/10.1071/ch10086.

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The development of the chemistry of benzyne and of arynes under flash vacuum pyrolytic conditions was strongly influenced by a parallel study of the chemistry of propadienones, and by the discovery of the acetylene/methylenecarbene rearrangement. A limited range of typical aryne reactions studied at The Australian National University and at Monash University from 1965 to 1996 is described, and pathways of aryne formation are considered.

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Lee, Daesung, and Sourav Ghorai. "Aryne-Based Multicomponent Coupling Reactions." Synlett 31, no. 08 (March 20, 2020): 750–71. http://dx.doi.org/10.1055/s-0039-1690824.

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Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

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Idiris, Fahima I. M., and Christopher R. Jones. "Recent advances in fluoride-free aryne generation from arene precursors." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9044–56. http://dx.doi.org/10.1039/c7ob01947e.

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Aryne chemistry has flourished in the past few decades. This review highlights new aryne precursors that operate under fluoride-free conditions as alternative methodologies to the popular fluoride-mediated ortho-silylaryl triflates.

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Martin, Nelson, and Ruchi Bharti. "Arynes in Natural Product Synthesis." International Journal for Research in Applied Science and Engineering Technology 11, no. 4 (April 30, 2023): 2633–44. http://dx.doi.org/10.22214/ijraset.2023.50703.

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Abstract: Arynes are a unique class of intermediates used in synthetic organic chemistry, and research interest has been intensely focused on their peculiar reactivities. Arynes have been researched for almost a century. However, difficulties in monitoring these reactive species, as well as difficulties in creating synthetically viable techniques for their synthesis and trapping, have restricted their application. A key tactic for achieving the racemic and enantiopure total synthesis of a broad variety of natural compounds or their structural derivatives. The chemistry of arynes has advanced significantly over the past thirty years, particularly in the field of transition metal carbon- carbon and carbon-heteroatom bond-forming mechanisms. The field’s fast growth is largely attributable to the development of mild aryne production processes. To create a natural product with complex organic molecules, the role of aryne intermediates was non-replaceable. These organic substances are often used in medicine, therapies, or as raw material for the synthesis of other substances. Moreover, they may perform important biological tasks. There are numerous methods for synthesizing natural compounds including total synthesis, semi-synthesis, and biosynthesis. Total synthesis is the process of creating natural products entirely chemically from basic precursors as well as it can be produced in large quantities and can reveal information about its biological activity. One of the developments in Arynes’ chemistry is the chemical rearrangements brought about by this electrophilic intermediate. It is not feasible to use conventional methods in a single step. This review article discusses how arynes are used to create natural products. Arynes has a wide range of functionality in the field of scientific research. The evolution of this method has made a tremendous change in the total synthesis of natural products. Benzynes enabled creative synthesis in mild conditions. The transformation has expanded to investigate various reaction classes such as nucleophilic addition, (4+2), and (2+2) cycloaddition strategies and metal-catalyzed reactions are shown and explained in this article. This review will provide an idea about how the arynes act as an intermediate in those reaction mechanisms and enlighten the scope of these aryne intermediate.

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Neog, Kashmiri, and Pranjal Gogoi. "Recent advances in the synthesis of organophosphorus compounds via Kobayashi's aryne precursor: a review." Organic & Biomolecular Chemistry 18, no. 47 (2020): 9549–61. http://dx.doi.org/10.1039/d0ob01988g.

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Ito, Motoki, Yuka Yamabayashi, Mio Oikawa, Emi Kano, Kazuhiro Higuchi, and Shigeo Sugiyama. "Silica gel-induced aryne generation from o-triazenylarylboronic acids as stable solid precursors." Organic Chemistry Frontiers 8, no. 12 (2021): 2963–69. http://dx.doi.org/10.1039/d1qo00385b.

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We developed o-triazenylarylboronic acids as stable solid aryne precursors, which generate arynes under mild conditions using silica gel as the sole reagent and undergo reactions with a range of arynophiles both in solution and in the solid-state.

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Tanaka, Hideya, Hitoshi Kuriki, Teruhiko Kubo, Itaru Osaka, and Hiroto Yoshida. "Copper-catalyzed arylstannylation of arynes in a sequence." Chemical Communications 55, no. 46 (2019): 6503–6. http://dx.doi.org/10.1039/c9cc02738f.

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Diverse ortho-stannylbiaryls and teraryls have been synthesized by copper-catalyzed arylstannylation of arynes, in which the single or dual insertion of arynes into arylstannanes is precisely controllable by simply changing the equivalence of the aryne precursors employed.

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Nakajima, Hana, Yuki Hazama, Yuki Sakata, Keisuke Uchida, Takamitsu Hosoya, and Suguru Yoshida. "Diverse diaryl sulfide synthesis through consecutive aryne reactions." Chemical Communications 57, no. 21 (2021): 2621–24. http://dx.doi.org/10.1039/d0cc08373a.

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Wenk, Hans Henning, Michael Winkler, and Wolfram Sander. "One Century of Aryne Chemistry." Angewandte Chemie International Edition 42, no. 5 (February 3, 2003): 502–28. http://dx.doi.org/10.1002/anie.200390151.

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Mhaske, Santosh, and Ranjeet Dhokale. "Transition-Metal-Catalyzed Reactions Involving Arynes." Synthesis 50, no. 01 (November 22, 2017): 1–16. http://dx.doi.org/10.1055/s-0036-1589517.

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Анотація:

The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

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Дисертації з теми "Aryne Chemistry"

Cant, Alastair Alexander. "Investigations into aryne chemistry." Thesis, University of Edinburgh, 2012. http://hdl.handle.net/1842/6249.

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The first project in this thesis describes our research reacting arynes with tertiary allyl amines to generate functionalised anilines via a benzyne induced aza-Claisen reaction. This process works in good to excellent yields and the methodology can be further applied to make benzannulated medium sized ring amine systems. The second project covered in this thesis details our studies in the generation of benzyne from benzoic acid. This process utilises palladium catalysis involving an ortho C-H activation of benzoic acid which generates a 5 membered palladacycle. This palladacycle then spontaneously decomposes with heat to generate palladium bound benzyne and carbon dioxide. The yield of benzyne was monitored by observing the amount of triphenylene formed in the process. Further synthetic applications in this process were limited, but it was shown that the benzyne could be reacted with alkynes to generate phenanthrene and naphthalene products. The third project in this thesis details our work on the insertion of benzyne into the C–S bond of thioesters. Using palladium catalysis and an o-trimethylsilylphenyl triflate benzyne precursor, a variety of thioethers were produced. The yields for this reaction were moderate to good but it was found that only aromatic substituents were tolerated on the thioester.

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Liu, Zhijian. "Novel aryne chemistry in organic synthesis." [Ames, Iowa : Iowa State University], 2006.

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Pocock, Ian. "Novel cascade aryne-capture/rearrangement reactions." Thesis, University of Huddersfield, 2014. http://eprints.hud.ac.uk/id/eprint/23743/.

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Arynes are reactive intermediates that have been an academic curiosity for over a century. A recent renaissance of interest in the chemistry of these intermediates can be traced back to the development of ortho-(silyl)aryl triflates as aryne precursors. The application of aryne chemistry outside academia has been precluded by the expense and laborious preparation of these precursors. Diphenyliodonium-2-carboxylate has been shown to be a stable and inexpensive benzyne precursor, however application has been limited due to the high temperature (>160 ºC) and long reaction times required to generate benzyne by this protocol. Described within is an investigation whereby diphenyliodonium-2-carboxylate is successfully decomposed using microwave irradiation to generate benzyne. This proof of concept investigation shows diphenyliodonium-2-carboxylate can be applied as an off-the-shelf benzyne precursor; by using microwave radiation, significantly reduced reaction times and lower b.p. solvents can facilitate a more universal application of this protocol than previously described. The investigation into the reactions of allylamino malonates with arynes is also described. Simple allylamino malonates are shown to perform a novel cascade aryne capture/ring-closure/[2,3]-rearrangement to generate indolin-3-one products. The influence of substitution of the indolin-3-one products on the photophysical properties is probed. Tetrahydropyridine derived aminomalonates result in a ring contraction by [2,3]-rearrangement to N-phenyl pyrrolidine products. Further investigations show N-allyl proline methyl esters also generate indolin-3-one products by this novel cascade mechanism. The photophysical properties of these products are also probed. N-diallylalanine methyl ester is shown to generate indolin-3-one with benzyne however N-allyl sarcosine ethyl ester generates the N-phenyl -allylated amino esters product by aryne capture/[2,3]-rearrangement.

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Manikandan, T. "Extending aryne chemistry: coupling benzynes with tropones, alocohols, azirines, allylthioethers and more." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2017. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/3933.

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Dhokale, R. A. "Development of novel methodologies in Aryne chemistry and their application in the total synthesis of bioactive natural products." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2018. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/4351.

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The present thesis demonstrates a creative exploration of aryne as versatile building blocks to construct new C–C and C–heteroatom bonds for the synthesis of various scaffolds and complex natural products. Chapter 1 describes a brief history of aryne, different methods available for their generation and various types of aryne reactions. Representative examples of insertion, pericyclic, annulation and multicomponent reactions of aryne are described in detail. Chapter 2 deals with our studies on C–C, C–P and C–N bond forming reactions of aryne, which is divided into three sections. Section 1 covers the transition-metal-free C–arylation of malonamide esters. We have achieved a selective mono- or di-arylation and quaternary centre generation using arynes. Section 2 demonstrates a novel process for C–P bond construction to afford aryl phosphonates, -phosphinates and phosphine oxides for the first time using transition-metal-free protocol. Section 3 describes an unusual nucleophilic nitration protocol using aryne chemistry, and the concept has been further extended for the synthesis of ortho-difuntionalized nitro-aromatics via a multicomponent reaction. Chapter 3 describes our studies on the total synthesis of bioactive natural products using aryne in two sections. Section 1 deals with the synthesis of the spiroannulated benzofuran-3-one scaffold of Leptosphaerins C and congeners via insertion reaction of aryne, whereas section 2 covers the study towards the total synthesis of Lycorane family of natural products via cycloaddition reaction of aryne.
AcSIR

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Lin, Wenwei. "Preparation of Polyfunctionalized Grignard Reagents and their Application in Aryne Chemistry." Diss., [S.l.] : [s.n.], 2006. http://edoc.ub.uni-muenchen.de/archive/00006045.

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Schwan, Johannes [Verfasser]. "Step Efficient Synthesis of 3,4-Dioxygenated Quinolones Enabled by Aryne Chemistry / Johannes Schwan." Berlin : Freie Universität Berlin, 2020. http://d-nb.info/1219904783/34.

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Pandya, V. "Transition-metal-free access to biologically important scaffolds via novel C–C and C–X bond formations using aryne chemistry." Thesis(Ph.D.), National Chemical Laboratory, Pune, 2019. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/5841.

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The present thesis demonstrates the importance of aryne in the construction of C–C, C–S, and C–N bonds, which result in the synthesis of the biologically important scaffolds. Chapter 1 presents the introduction of aryne and its mode of reactivity especially leading to the difunctionalization of arenes. It comprises insertion, pericyclic, annulation and multicomponent reactions of aryne and their representative examples. Chapter 2 deals with difunctionalization of aryne to form sulfones and xanthones, which is further divided into two sections. Section 1 presents the transition-metal-free synthesis of sulfones using aryne chemistry. We were able to synthesize diaryl as well as alkyl aryl sulfones in excellent yields. Section 2 reveals the effort towards the total synthesis of diversonol natural product. Chapter 3 demonstrates the novel process for the synthesis of varyingly substituted oxindolylidene acetates in good yields. This method has been further extended to the one-pot synthesis of spiroxindolopyrrolidones. Chapter 4 describes the utilization of aryne in the general synthesis of octahydroquinoline scaffold in a stereoselective manner.
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Bhunia, A. "Transition-metal-free carbon-carbon and carbon-heteroatom bond - forming reactions using N -heterocyclic carbene organocatalysis and aryne chemistry." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2016. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2074.

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Jawade, K. "Synthesis of naturally occurring polyhydroxylated δ--lactones, aryne mediated synthesis of phenyl indolines and pd-sba-tat catalyzed c-c cross coupling reactions". Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2018. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/5868.

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Книги з теми "Aryne Chemistry"

Mortier, Jacques, ed. Arene Chemistry. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.

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D, Astruc, ed. Modern arene chemistry. Weinheim: Wiley-VCH, 2002.

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Appelbe, Ruth. Synthetic applications of cationic arene-alkene cyclisations. Dublin: University College Dublin, 1997.

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Biju, Akkattu T. Modern Aryne Chemistry. Wiley & Sons, Incorporated, John, 2021.

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Biju, Akkattu T. Modern Aryne Chemistry. Wiley & Sons, Limited, John, 2021.

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Biju, Akkattu T. Modern Aryne Chemistry. Wiley & Sons, Incorporated, John, 2021.

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Biju, Akkattu T. Modern Aryne Chemistry. Wiley & Sons, Incorporated, John, 2021.

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Comprehensive Aryne Synthetic Chemistry. Elsevier, 2022. http://dx.doi.org/10.1016/c2020-0-01658-0.

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Yoshida, Hiroto. Comprehensive Aryne Synthetic Chemistry. Elsevier, 2022.

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Yoshida, Hiroto. Comprehensive Aryne Synthetic Chemistry. Elsevier, 2022.

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Частини книг з теми "Aryne Chemistry"

Sanz, Roberto, and Anisley Suárez. "The Chemistry of Arynes." In Arene Chemistry, 299–336. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch12.

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Winkler, Michael, Hans Henning Wenk, and Wolfram Sander. "Arynes." In Reactive Intermediate Chemistry, 741–94. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2005. http://dx.doi.org/10.1002/0471721492.ch16.

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Klumpp, Douglas A. "Electrophilic Aromatic Substitution." In Arene Chemistry, 1–31. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch1.

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Rossi, Roberto A., Javier F. Guastavino, and María E. Budén. "Radical-Nucleophilic Aromatic Substitution." In Arene Chemistry, 243–68. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch10.

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Mąkosza, Mieczysław. "Nucleophilic Substitution of Hydrogen in Electron-Deficient Arenes." In Arene Chemistry, 269–98. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch11.

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Foubelo, Francisco, and Miguel Yus. "Reduction/Hydrogenation of Aromatic Rings." In Arene Chemistry, 337–64. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch13.

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Kholdeeva, Oxana A. "Selective Oxidation of Aromatic Rings." In Arene Chemistry, 365–98. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch14.

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Pigge, F. Christopher. "Dearomatization Reactions." In Arene Chemistry, 399–423. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch15.

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Sankararaman, Sethuraman. "Aromatic Compounds Via Pericyclic Reactions." In Arene Chemistry, 425–49. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch16.

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de Koning, Charles B., and Willem A. L. van Otterlo. "Ring-Closing Metathesis." In Arene Chemistry, 451–84. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch17.

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Тези доповідей конференцій з теми "Aryne Chemistry"

Yus, M., J. Almena, E. Alonso, F. Alonso, A. Bachki, P. Choudhury, F. Foubelo, et al. "Functionalized Organolithium Compounds Through an Arene-Catalyzed Lithiation." In The 1st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1997. http://dx.doi.org/10.3390/ecsoc-1-02003.

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Gómez-Escalonilla, Maria José, Fernando Langa, Alejandro Criado, María Vizuete, Sergio García-Rodríguez, Jose Luis G. Fierro G. Fierro, Agustín Cobas, Diego Peña, and Enrique Guitián. "EfficientCycloaddition of Arynes to Carbon Nanotubes under Microwave Irradiation." In The 17th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2013. http://dx.doi.org/10.3390/ecsoc-17-c006.

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Yus, M., E. Alonso, F. Alonso, A. Bachki, K. Choudhury, F. Foubelo, C. Gomez, et al. "The Lithium-arene (cat.) System: New Applications to Organic Transformations." In The 2nd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1998. http://dx.doi.org/10.3390/ecsoc-2-01679.

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Yus, M., F. Alonso, P. Candela, C. Gomez, J. Gomis, A. Guijarro, F. Huerta, et al. "Nickel-promoted Reductive Cleavage of Nitrogen-nitrogen and Nitrogenoxygen Bonds Mediated by Lithium and a Catalytic Amount of an Arene or Polymer Supported Arene." In The 4th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2000. http://dx.doi.org/10.3390/ecsoc-4-01800.

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Kosgei, Gilbert, P. U. Ashvin Fernando, Harley R. McAlexander, Emilie Chapple, and Ryan M. O'Donnell. "Synergizing supramolecular chemistry and reverse saturable absorption: exploring pillar[5]arene with metal-complexed ligands." In Organic Photonic Materials and Devices XXVI, edited by Ileana Rau, Okihiro Sugihara, and William M. Shensky. SPIE, 2024. http://dx.doi.org/10.1117/12.3001913.

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Yus, M., E. Alonso, J. Ferrandez, F. Foubelo, I. Gomez, D. Guijarro, A. Gutierrez, et al. "Arene-Catalysed Reductive Cleavage of the Benzylic Carbon-Sulfur Bond: Generation of Benzylic Lithium Reagents." In The 4th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2000. http://dx.doi.org/10.3390/ecsoc-4-01801.

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Nayak, Manini, Kanyanjali Samal, and Anita Pati. "Synthesis and characterization of the rccc-isomer of dodecatriazolo-resorcin[4]arene cavitand." In 2ND INTERNATIONAL CONFERENCE ON EMERGING SMART MATERIALS IN APPLIED CHEMISTRY (ESMAC-2021): ESMAC-2021. AIP Publishing, 2023. http://dx.doi.org/10.1063/5.0127510.

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Vavilova, A. A., I. E. Shiabiev, P. L. Padnya, and I. I. Stoikov. "Synthesis and spatial structure of p-tert-butylthiacalix[4]arene derivatives containing amide and amino groups." In ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0075982.

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Radivoy, Gabriel, Francisco Alonso, Miguel Yus, Viviana Dorn, Adriana Pierini, Andrés Ciolino, Yanina Moglie, and Fabiana Nador. "Reductive amination of aldehydes using a lithium-arene(cat.) reducing system. A simple one-pot procedure for the synthesis of secondary amines." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00678.

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Yakimova, Luidmila, Aigul Nugmanova, Dmitry Shurpik, Pavel Padnya, Timur Mukhametzyanov, and Ivan Stoikov. "Micelleplexes and polyplexes with DNA from salmon sperm based on pillar[5]arenes and thiacalix[4]arene." In ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0069054.

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Звіти організацій з теми "Aryne Chemistry"

Liu, Zhijian. Novel Aryne Chemistry in Organic Synthesis. Office of Scientific and Technical Information (OSTI), December 2006. http://dx.doi.org/10.2172/897369.

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