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Автор: Grafiati

Опубліковано: 6 вересня 2023

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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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3

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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4

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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5

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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6

Yi, Chae S., та 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, № 15 (липень 1998): 3158–60. http://dx.doi.org/10.1021/om980405g.

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7

YI, C. S., та 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, № 46 (18 червня 2010): no. http://dx.doi.org/10.1002/chin.199846071.

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8

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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9

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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10

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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11

Stará, Irena G., Ivo Starý, Adrian Kollárovič, Filip Teplý, David Šaman, and Pavel Fiedler. "Coupling Reactions of ortho-Substituted Halobenzenes with Alkynes. The Synthesis of Phenylacetylenes and Symmetrical or Unsymmetrical 1,2-Diphenylacetylenes." Collection of Czechoslovak Chemical Communications 64, no. 4 (1999): 649–72. http://dx.doi.org/10.1135/cccc19990649.

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Анотація:

The Pd- or Pd/Cu-catalyzed coupling reactions of halobenzenes bearing the methyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl, or both methoxy and 4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl groups in the ortho-position with gaseous or metallated acetylene, (trialkylsilyl)acetylenes, and arylacetylenes have been systematically studied. Various functionalized aryl- or diarylacetylenes have been synthesized in good to excellent yields. Whereas additional fluoro, nitro, or methoxy group attached to the benzene ring does not interfere in the coupling reactions, the presence of a methoxycarbonyl requires a careful optimization of reaction conditions to achieve moderate yields.

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12

Li, Xiang, Ning Chen, and Jiaxi Xu. "Microwave-Assisted CuCl-Catalyzed Three-Component Reactions of Alkynes, Aldehydes, and Amino Alcohols." Synthesis 51, no. 17 (May 8, 2019): 3336–44. http://dx.doi.org/10.1055/s-0037-1611536.

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A microwave (MW)-assisted three-component coupling of amino alcohols, aldehydes, and alkynes is developed under catalysis by CuCl. Compared with thermal conditions, MW irradiation greatly increases the reaction efficiency. The reactions of various primary N-alkyl/arylamino alcohols, aliphatic/aromatic aldehydes, and alkynes are systematically investigated, affording the desired products in moderate to good yields. Notably, acetylene is also an effective reactant under the current MW-assisted conditions.

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13

Horstmann, Jan, Stefanie Reger, Beate Neumann, Hans-Georg Stammler, and Norbert W. Mitzel. "One-pot desilylation-Sonogashira coupling." Zeitschrift für Naturforschung B 72, no. 7 (June 27, 2017): 489–95. http://dx.doi.org/10.1515/znb-2017-0027.

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AbstractCoupling of diethynyldiphenylsilane (1) with aryl halides under Sonogashira conditions affords the symmetrical diarylacetylenes bis(2-methylpyridin-5-yl)acetylene (2), bis(4-fluorophenyl)acetylene (3) and bis(4-trifluoromethylphenyl)acetylene (4) in 60% to 82% yield. In the case of 2, the by-product bis(2-methylpyridin-5-yl)butadiyne (2a) was isolated in 12% yield. The occurring desilylation reaction was investigated by treating bis(phenylethynyl)diphenylsilane (5) under the same conditions. The formation of 1-fluoro-4-(phenylethynyl)benzene (6), 1-trifluoromethyl-4-(phenylethynyl)benzene (7) and (tetrafluoropyridin- 4-yl)ethynylbenzene (8) in 70 to 84% yield and the cleavage of hexaphenylcyclotrisiloxane were observed in all cases.

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14

Vasilevsky, S. F., and A. A. Stepanov. "FUNDAMENTAL AND APPLIED ASPECTS OF THE CHEMISTRY OF ACETYLENYLQUINONES." Resource-Efficient Technologies, no. 4 (February 27, 2020): 30–43. http://dx.doi.org/10.18799/24056537/2019/4/266.

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In addition to the reported synthetic routes for the acetylene derivatives of quinones, a detailed analysis of the fundamental chemical, physicochemical, and biological properties of this class of compounds is presented herein. The advantages of Pd- and Cu-catalyzed cross-coupling of terminal alkynes with iodarenes via the Sonogashira reaction to produce new acetylenylquinones with predetermined properties are examined. Here, combining quinoid and acetylene residues into one molecule gives the resulting compounds chemical specificity, as demonstrated by several reported examples of non-trivial transformations. In particular, the presence of the quinoid cycle significantly increases the electrophilicity of the triple bond and determines the range of transformation possibilities. Moreover, acetylenylquinones have heightened sensitivity to both external (such as the reaction temperature and the nature of the solvent) and internal (e.g., the structure of substituents in the nucleus and the acetylene fragment) factors. For example, regioselective cleavage of a strong triple bond under the action of amines is possible in the absence of a metal catalyst. Peri-substituted acetylenyl-9,10-anthraquinones are most suited for the synthetic route because of the proximity of the acetylene and carbonyl groups. Mechanisms of reactions of selective alkynylquinones are described.

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15

Vasilevsky, S. F., and A. A. Stepanov. "FUNDAMENTAL AND APPLIED ASPECTS OF THE CHEMISTRY OF ACETYLENYLQUINONES." Resource-Efficient Technologies, no. 4 (February 27, 2020): 30–43. http://dx.doi.org/10.18799/24056529/2019/4/266.

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Анотація:

In addition to the reported synthetic routes for the acetylene derivatives of quinones, a detailed analysis of the fundamental chemical, physicochemical, and biological properties of this class of compounds is presented herein. The advantages of Pd- and Cu-catalyzed cross-coupling of terminal alkynes with iodarenes via the Sonogashira reaction to produce new acetylenylquinones with predetermined properties are examined. Here, combining quinoid and acetylene residues into one molecule gives the resulting compounds chemical specificity, as demonstrated by several reported examples of non-trivial transformations. In particular, the presence of the quinoid cycle significantly increases the electrophilicity of the triple bond and determines the range of transformation possibilities. Moreover, acetylenylquinones have heightened sensitivity to both external (such as the reaction temperature and the nature of the solvent) and internal (e.g., the structure of substituents in the nucleus and the acetylene fragment) factors. For example, regioselective cleavage of a strong triple bond under the action of amines is possible in the absence of a metal catalyst. Peri-substituted acetylenyl-9,10-anthraquinones are most suited for the synthetic route because of the proximity of the acetylene and carbonyl groups. Mechanisms of reactions of selective alkynylquinones are described.

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16

Scattergood, Paul A., Milan Delor, Igor V. Sazanovich, Michael Towrie, and Julia A. Weinstein. "Ultrafast charge transfer dynamics in supramolecular Pt(ii) donor–bridge–acceptor assemblies: the effect of vibronic coupling." Faraday Discussions 185 (2015): 69–86. http://dx.doi.org/10.1039/c5fd00103j.

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Thanks to major advances in laser technologies, recent investigations of the ultrafast coupling of nuclear and electronic degrees of freedom (vibronic coupling) have revealed that such coupling plays a crucial role in a wide range of photoinduced reactions in condensed phase supramolecular systems. This paper investigates several new donor–bridge–acceptor charge-transfer molecular assemblies built on a trans-Pt(ii) acetylide core. We also investigate how targeted vibrational excitation with low-energy IR light post electronic excitation can perturb vibronic coupling and affect the efficiency of electron transfer (ET) in solution phase. We compare and contrast properties of a range of donor–bridge–acceptor Pt(ii) trans-acetylide assemblies, where IR excitation of bridge vibrations during UV-initiated charge separation in some cases alters the yields of light-induced product states. We show that branching to multiple product states from a transition state with appropriate energetics is the most rigid condition for the type of vibronic control we demonstrate in our study.

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17

Bai, Donghu, Chunju Li, Jian Li, and Xueshun Jia. "New Progress of Acetylene-Coupling Reactions." Chinese Journal of Organic Chemistry 32, no. 6 (2012): 994. http://dx.doi.org/10.6023/cjoc1202073.

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18

Miao, Zong Cheng, Yi Wei Wang, Yuan Yuan Li, Lei Zhang, Xin Zhang, and Zhi Xue Wang. "Synthesis of LC Intermediate Containing Trimethyl Silyl Acetylene Group." Advanced Materials Research 781-784 (September 2013): 280–82. http://dx.doi.org/10.4028/www.scientific.net/amr.781-784.280.

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In order to obtain the important liquid crystal intermediate with trifluoromethyl substitutent, Sonogashira coupling reaction was used to synthesize the compound. In this paper, the intermediate was synthesized by 4'-Iodo-4-pentyl-biphenyl and trimethyl silyl acetylene (TMSA) as raw materials. During the synthesis, the optimum reaction conditions were obtained, that the mol ratio of 4'-Iodo-4-pentyl-biphenyl and trimethyl silyl acetylene is 1:2, the reaction temperature is 30 oC, and the reaction time is 10 h.

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19

Asomoza-Solís, Eric Omar, Jonathan Rojas-Ocampo, Rubén Alfredo Toscano, and Susana Porcel. "Arenediazonium salts as electrophiles for the oxidative addition of gold(i)." Chemical Communications 52, no. 45 (2016): 7295–98. http://dx.doi.org/10.1039/c6cc03105f.

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Arenediazonium salts have been found to behave as efficient electrophiles for the oxidation of gold(i). Starting from anilines, a one pot cross-coupling reaction of anilines with silver acetylides mediated by gold has been developed.

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20

Tarasov, Maxim V., Olga D. Bochkova, Tatyana V. Gryaznova, Asiya R. Mustafina, and Yulia H. Budnikova. "Non-Noble-Metal Mono and Bimetallic Composites for Efficient Electrocatalysis of Phosphine Oxide and Acetylene C-H/P-H Coupling under Mild Conditions." International Journal of Molecular Sciences 24, no. 1 (January 1, 2023): 765. http://dx.doi.org/10.3390/ijms24010765.

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The present work describes an efficient reaction of electrochemical phosphorylation of phenylacetylene controlled by the composition of catalytic nanoparticles based on non-noble-metals. The sought-after products are produced via the simple synthetic protocol based on room temperature, atom-economical reactions, and silica nanoparticles (SNs) loaded by one or two d-metal ions as nanocatalysts. The redox and catalytic properties of SNs can be tuned with a range of parameters, such as compositions of the bimetallic systems, their preparation method, and morphology. Monometallic SNs give phosphorylated acetylene with retention of the triple bond, and bimetallic SNs give a bis-phosphorylation product. This is the first example of acetylene and phosphine oxide C-H/P-H coupling with a regenerable and recyclable catalyst.

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21

Nauš, Petr, Ivan Votruba, and Michal Hocek. "Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides." Collection of Czechoslovak Chemical Communications 69, no. 10 (2004): 1955–70. http://dx.doi.org/10.1135/cccc20041955.

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Анотація:

The title bis(purin-6-yl)acetylene and -diacetylene nucleoside derivatives were prepared as covalent base-pair analogues starting from acyl-protected 6-ethynylpurine and 6-iodopurine nucleosides by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by deprotection. The key starting acyl-protected 6-ethynylpurine nucleosides were prepared by a sequence of cross-coupling reactions of protected 6-halopurine nucleosides with (trimethylsilyl)acetylene followed by a modified desilylation with TBAF in presence of acetic acid. Surprisingly, the acyl-protected nucleosides exhibited significant cytostatic activity higher than the fully deprotected title compounds.

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22

Voronin, Vladimir V., Maria S. Ledovskaya, Alexander S. Bogachenkov, Konstantin S. Rodygin, and Valentine P. Ananikov. "Acetylene in Organic Synthesis: Recent Progress and New Uses." Molecules 23, no. 10 (September 24, 2018): 2442. http://dx.doi.org/10.3390/molecules23102442.

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Анотація:

Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule.

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23

Akita, Munetaka, Masako Terada та Yoshihiko Moro-oka. "Photochemical C–C coupling reaction of an iron acetylide complex [Fe(η5-C5Me5)(CO)2(C CPh)] with alk-1-ynes (RCCH) leading to cyclic compounds including paramagnetic iron(i) cyclopentadienone complexes [Fe(η5-C5Me5)(η4-2-Ph -5-R-C5H2O)]". Chemical Communications, № 3 (1997): 265–66. http://dx.doi.org/10.1039/a606836g.

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24

Huo, Xiao Ping, Qi Pei Xu, and Zong Cheng Miao. "Synthesise of (4-Ethynyl-Phenyl)-(4-trifluoromethyl-phenyl)-Diazene, a Novel Intermediate of Azobenzene Liquid Crystal with High Birefrigence." Applied Mechanics and Materials 584-586 (July 2014): 1705–8. http://dx.doi.org/10.4028/www.scientific.net/amm.584-586.1705.

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Анотація:

In order to obtain an important azobenzene liquid crystal intermediate with phenylacetylene group, Sonogashira coupling reaction was used to preparation the compound. In this paper, the intermediate was synthesized by (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene (TMSA) as raw materials, and then the trimethyl silyl group was removaled under the action of K2CO3. During the synthesis, the optimum reaction conditions were obtained, that the mol ratio of (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene was 1:2, the reaction temperature was 80 oC. Fourier transform infrared spectroscopy (FT-IR) was used to measure the molecular structure of the target compound.

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25

Kiefer, Gregor, Barnali Dutta, Euro Solari, Rosario Scopelliti, and Kay Severin. "RhCl3-Mediated Coupling Reactions of tert-Butyl Acetylene." Zeitschrift für anorganische und allgemeine Chemie 638, no. 7-8 (February 22, 2012): 1114–18. http://dx.doi.org/10.1002/zaac.201100537.

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26

Heravi, Majid M., Mahzad Dehghani, Vahideh Zadsirjan, and Manijheh Ghanbarian. "Alkynes as Privileged Synthons in Selected Organic Name Reactions." Current Organic Synthesis 16, no. 2 (March 26, 2019): 205–43. http://dx.doi.org/10.2174/1570179416666190126100744.

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Background:Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddtion via Click reaction, Sonogashira reaction, and Hetero Diels-Alder reaction.Objective:In this review, we try to underscore the applications of alkynes as privileged synthons in the formation of heterocycles, focused on the selected reactions of alkynes as a synthon or impending utilization in synthetic organic chemistry, which have reached such high status for being included in the list of name reactions in organic chemistry.Conclusion:Alkynes (including acetylene) are an unsaturated hydrocarbon bearing one or more triple C-C bond. Remarkably, alkynes and their derivatives are frequently being used as molecular scaffolds for planning new organic reactions and installing reactive functional group for further reaction. It is worth mentioning that in general, the terminal alkynes are more useful and more frequently being used in the art of organic synthesis. Remarkably, alkynes have found different applications in pharmacology, nanotechnology, as well as being known as appropriate starting precursors for the total synthesis of natural products and biologically active complex compounds. They are predominantly applied in various name reactions such as Sonogashira, Glaser reaction, Friedel-crafts reaction, Castro-Stephens coupling, Huisgen 1.3-dipolar cycloaddtion reaction via Click reaction, Sonogashira reaction, hetero-Diels-Alder reaction. In this review, we tried to impress the readers by presenting selected name reactions, which use the alkynes as either stating materials or precursors. We disclosed the applications of alkynes as a privileged synthons in several popular reactions, which reached to such high status being classified as name reactions. They are thriving and well known and established name reactions in organic chemistry such as Regioselective, 1,3-dipolar Huisgen cycloaddtion reaction via Click reaction, Sonogashira reaction and Diels-Alder reaction.

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27

Filippou, Alexander Constantin, and Walter Grünleitner. "Säure-induzierte CC-Kupplung von Isocyanid-Liganden in homoleptischen Alkylisocyanid-Komplexen von Mo(0) und W(0) / Acid-Induced CC-Coupling of Isocyanide Ligands in Homoleptic Alkylisocyanide Complexes of Mo(0) and W(0)." Zeitschrift für Naturforschung B 46, no. 2 (February 1, 1991): 216–30. http://dx.doi.org/10.1515/znb-1991-0216.

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Reactions of the electron-rich, homoleptic alkylisocyanide complexes M(R N C)6 (1a-2b) (1: M = Mo, 2: M = W; a: R = Et, b: R = tBu) with electrophiles have been studied. A coupling of two isocyanide ligands to a complexed alkyne ligand is observed, when M(R N C)6 is treated with two equivalents of HX(X = Br, I) and leads to the bis(alkylamino)acetylene complexes [X (R N C )4M[η2-R(H)NC ≡ CN(H)R]]X (3a′-4b″) (3: M = Mo, 4: M = W). Treatment of W (EtNC)6 (2a) and W (tBuNC)6 (2b) with one equivalent of Me3SiOTf results in the quantitative formation of the aminocarbyne complexes [(EtNC)5W ≡ CN (SiMe3)Et]OTf (6c) and [(tBuNC)5W ≡ C N (SiMe3)tBu]OTf (6d), respectively. In comparison, an equilibrium between W(tBuNC)6 (2b) and the aminocarbyne complex [(tBuNC)5W ≡ C N (SiMe3)tBu]Cl (6e) is found, when 2b is treated with Me3SiCl. The compounds 6c and 6d are structurally related to the aminocarbyne complexes [(EtNC)5M ≡ C N E t2]BF4 (5a: M = Mo, 6a: M = W) and [(tBuNC)5W ≡ C N (Et)Bu]BF4 (6b), which are obtained from ethylation of M (EtNC)6 (1a, 2a) and W (tBuNC)6 (2b) with Et3OBF4. 5a and 6a undergo with HI a carbyne-isocyanide coupling reaction to give the alkyne complexes [I(EtNC)4Mo[η2-Et2NC≡CN(H)Et]]BF4 (7a) and [I(EtNC)4W[η2-Et2NC≡CN(H)Et]]BF4 (8a), respectively. Similar reactivity is exhibited by 6b, which yields with HI the alkyne complex [I(tBuNC)4W[η2-tBu(Et)N C ≡ C N (H)tBu]]BF4 (8b). The reported transformation of a complexed isocyanide to an aminocarbyne and the acid-induced aminocarbyne-isocyanide coupling reaction are experimentally verified to be important steps in the reductive coupling of isocyanide ligands in [M(RNC)6X]+-complexes yielding the bis(alkylamino)acetylene compounds [X(R N C)4M[η2-R (H )N C ≡ C N (H )R ]]+.

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28

Ogawa, Narihito, Shinsaku Sone, Song Hong, Yan Lu, and Yuichi Kobayashi. "Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid." Synlett 31, no. 17 (August 17, 2020): 1735–39. http://dx.doi.org/10.1055/s-0040-1706415.

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The C16–C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11–C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1–C10 segment and Boland reduction using Zn with TMSCl.

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29

Zhang, Yong Ming, Yi Wei Wang, Dan Dan Dang, Jie Si, Jian Fang Liu, and Mei Zhang. "Liquid Crystal Phase Behavior of Novel Mesogenic Compound with Trifluoromethyl Substitutent." Advanced Materials Research 785-786 (September 2013): 680–83. http://dx.doi.org/10.4028/www.scientific.net/amr.785-786.680.

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In order to obtain a novel liquid crystal compound with trifluoromethyl substitutent, Sonogashira coupling reaction was used to synthesize the mesogenic compound based on tolane. Firstly, 1-iodo-4-trifluoromethyl-benzene was modified with acetylene groups, and then coupled with iodo amyl biphenyl through Sonogashira reaction to obtain the target compound. Moreover, the liquid crystal phase behaviors including transition temperatures and phase sequences were investigated by DSC and POM.

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30

Sharada, Ambati, Lakshmi Srinivasa Rao Kundeti, Kallaganti V. S. Ramakrishna, and Kommu Nagaiah. "First Stereoselective Total Synthesis of Ciryneol C." SynOpen 03, no. 02 (April 2019): 59–66. http://dx.doi.org/10.1055/s-0037-1611876.

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The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

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31

Nguyen Thi Minh, Trang, Trang Tran Thi Thu, and Hoan Duong Quoc. "REACTION OF SOME SALICYL ALDEHYDE DERIVATIVES WITH AMINES ANDPHENYL ACETYLENE." Journal of Science Natural Science 65, no. 10 (October 2020): 61–66. http://dx.doi.org/10.18173/2354-1059.2020-0048.

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Salicylic aldehydes, amine, and phenyl acetylene could react under the solvent-free, metal-free conditions to form propargylamines 1-4 via A3 coupling reaction. The yield of the reaction was up to 83% for 5h. In acetonitrile, the amine became a catalyst to form 6-bromo-3-(5-bromo-2-hydroxybenzyl)-2-phenyl-4Hchromen-4-one (5). Under microwave conditions, it took about 20 min to complete the reaction and gave the same yields as theconventional method. Structures of these compounds were firm with NMR, MS spectra.

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32

Wang, Mingcun, Ming Yang, Tong Zhao, and Jian Pei. "Acetylene-grafted resins derived from phenolics via azo coupling reaction." European Polymer Journal 44, no. 3 (March 2008): 842–48. http://dx.doi.org/10.1016/j.eurpolymj.2008.01.002.

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33

Toda, Fumio, and Yoshihisa Tokumaru. "Oxidative Coupling Reaction of Acetylene Compounds in the Solid State." Chemistry Letters 19, no. 6 (June 1990): 987–90. http://dx.doi.org/10.1246/cl.1990.987.

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34

Sobenina, Lyubov’ N., and Boris A. Trofimov. "Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media." Molecules 25, no. 11 (May 27, 2020): 2490. http://dx.doi.org/10.3390/molecules25112490.

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The publications covering new, transition metal-free cross-coupling reactions of pyrroles with electrophilic haloacetylenes in solid medium of metal oxides and salts to regioselectively afford 2-ethynylpyrroles are discussed. The reactions proceed at room temperature without catalyst and base under solvent-free conditions. These ethynylation reactions seem to be particularly important, since the common Sonogashira coupling does not allow ethynylpyrroles with strong electron-withdrawing substituents at the acetylenic fragments to be synthesized. The results on the behavior of furans, thiophenes, and pyrazoles under the conditions of these reactions are also provided. The reactivity and structural peculiarities of nucleophilic addition to the activated acetylene moiety of the novel C-ethynylpyrroles are considered.

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35

Nematpour, Manijeh, Nafiseh Karimi, and Mohammad Mahboubi-Rabbani. "Copper-Catalyzed Ultrasonic-Promoted Coupling of Acetylene Analogs, Dialkyl azo dicarboxylate, and Benzazoles to Assemble Tricyclic Fused- Ring [1,2,3]triazolo[3,4-b][1,3]benzazole Analogs." Letters in Organic Chemistry 19, no. 1 (January 2022): 2–8. http://dx.doi.org/10.2174/1570178618666211001120336.

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: An unprecedented copper-catalyzed reaction of acetylene analogs with dialkyl azo dicarboxylate and benzazole analogs via a cross-coupling sequence was reported. A library of triazolobenzazole fused ring systems including [1,2,3] triazolo [3,4-b] [1,3] benzothiazole, [1,2,3] triazolo [3,4-b] [1,3] benzoxazole and [1,2,3] triazolo[3,4-b][1,3]benzimidazole structures were obtained in moderate to excellent yields under very mild reaction conditions. Structural confirmation of the final products became possible using different methods like spectroscopy and elemental analysis. The control experiments indicated C-H activation of acetylene by copper salts, followed by cycloaddition between a 2-(phenylethynyl)benzo[d]azol-3(2H)-yl anion and azo dicarboxylate as the key mechanistic feature. The broad substrate scope with simple and easily affordable starting materials, as well as mild reaction conditions are the noticeable attributes of this methodology, which provides facile access to the desired products.

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36

Kashiwagi, Yoshitomo, Shinya Chiba, Hiroshi Ikezoe, and Jun-ichi Anzai. "Polypyrrole-Supported Graphite Felt for Acetylene Coupling Reaction in Solid Phase." Synlett 2004, no. 14 (October 20, 2004): 2513–16. http://dx.doi.org/10.1055/s-2004-834835.

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37

Suades, Joan, Francoise Dahan, and Rene Mathieu. "Two-electron reduction of Fe3(CO)9(.mu.3-CCH2R)(.mu.3-COC2H5) complexes: induction of an alkylidyne-alkylidyne coupling reaction and of a subsequent rearrangement to acetylide or allenyl ligands. X-ray structure of [PPh4][Fe3(CO)9(.mu.3-.eta.3-C(OC2H5):C:CHC(O)CH3)] at 100 K." Organometallics 7, no. 1 (January 1988): 47–51. http://dx.doi.org/10.1021/om00091a009.

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38

Biswas, Nripendra Nath, George M. Iskander, Marcin Mielczarek, Tsz Tin Yu, David StC Black, and Naresh Kumar. "Alkyne-Substituted Fimbrolide Analogues as Novel Bacterial Quorum-Sensing Inhibitors." Australian Journal of Chemistry 71, no. 9 (2018): 708. http://dx.doi.org/10.1071/ch18194.

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Gram-negative bacteria such as Pseudomonas aeruginosa use furanosyl diesters as autoinducers for quorum sensing (QS), a major regulatory and cell-to-cell communication system for social adaptation, virulence factor production, biofilm formation, and antibiotic resistance. A range of natural and synthetic brominated furanones, i.e. fimbrolide derivatives, have been found to act as inhibitors of QS-dependent bacterial phenotypes, complementing the bactericidal ability of traditional antibiotics. In this work, several novel acetylene analogues of fimbrolides were synthesised in moderate to high yields via Sonogashira coupling reactions of brominated furanones 4-bromo-5-(bromomethylene)furan-2(5H)-one 4 and 5-(dibromomethylene)-3-ethylfuran-2(5H)-one 5. The Sonogashira reaction of acetylenes on 4-bromo-5-(bromomethylene)furan-2(5H)-one 4 was favoured at the C5 methylene bromide over the C4 bromide substituent. On biological testing, the most potent compounds 13 and 14 showed 82 and 98 % bacterial quorum-sensing inhibitory (QSI) activity against Pseudomonas aeruginosa reporter strain respectively.

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39

Ye, Xinglin, Pingping Wang, and Mingzhong Cai. "A General approach to Difunctionalised 1,3-dienes containing Silicon and Halogen via Hydrozirconation of (Z)-3-(trimethylsilyl)alk-3-en-1-ynes." Journal of Chemical Research 2007, no. 6 (June 2007): 319–22. http://dx.doi.org/10.3184/030823407x218039.

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Sonogashira coupling of ( E)-α-iodovinylsilanes 1 with (trimethylsilyl)acetylene gave ( Z)-1,3-bis(trimethylsilyl)alk-3-en-1-ynes 2, which underwent a desilylation reaction to afford ( Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3 in high yields. (1 E,3 Z)-1-Halo-3-(trimethylsilyl)-substituted 1,3-dienes 5 could be synthesised stereoselectively via hydrozirconation of ( Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3, followed by trapping with iodine or N-bromosuccinimide.

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40

Sakamoto, Takao, Akito Yasuhara, Yoshinori Kondo, and Hiroshi Yamanaka. "Palladium-Catalyzed Cross-Coupling Reaction of Ethoxy(tributylstannyl)acetylene with Aryl Iodides." Synlett 1992, no. 06 (1992): 502. http://dx.doi.org/10.1055/s-1992-21393.

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41

Dogan Demir, Kubra, Baris Kiskan, and Yusuf Yagci. "Thermally Curable Acetylene-Containing Main-Chain Benzoxazine Polymers via Sonogashira Coupling Reaction." Macromolecules 44, no. 7 (April 12, 2011): 1801–7. http://dx.doi.org/10.1021/ma1029746.

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42

TODA, F., and Y. TOKUMARU. "ChemInform Abstract: Oxidative Coupling Reaction of Acetylene Compounds in the Solid State." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145133.

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43

Hu, Xiao Dan, Shao Hong Wang, and Zhao Xia Hou. "Synthesis and Luminescent Properties of New Oligofluorene Derivatives Containing Various Comonomers." Advanced Materials Research 314-316 (August 2011): 2227–31. http://dx.doi.org/10.4028/www.scientific.net/amr.314-316.2227.

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Two kinds of oligofluorenes containing acetylene units are synthesized by Sonogashira coupling reaction. naphthalene and anthracene are co-polymerized with ethynylfluorene, respectively. The structure and properties are characterized using NMR, UV-vis spectroscopy, elemental analysis, DSC and photoluminescence. The oligomers are soluble in common organic solvents such as benzene and easily spin-coated onto glass substrates. The products yield strong emission differing from blue to green-yellow, and red-shift are suppressed with the growth in size of co-monomers.

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44

Leeming, Michael G., George N. Khairallah, Sandra Osburn, Krista Vikse, and Richard A. J. O'Hair. "Cobalt-Mediated Decarboxylative Homocoupling of Alkynyl Carboxylic Acids." Australian Journal of Chemistry 67, no. 5 (2014): 701. http://dx.doi.org/10.1071/ch13564.

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Cobalt-mediated decarboxylative Glaser-like C–C bond coupling of carboxylates has been studied in the gas phase using collision-induced dissociation (CID) multistage mass spectrometry (MSn) experiments. Both the identity of the carboxylate RCO2– (R = Me, HC≡C, MeC≡C, and PhC≡C) and the nuclearity of the complex ([CoCl(O2CR)2]– versus [Co2Cl3(O2CR)2]–) play a role in the types of reactions observed and their relative activation energies. In the first stage of CID, the mononuclear complex [CoCl(O2CMe)2]– undergoes decarboxylation, while the dinuclear [Co2Cl3(O2CMe)2]– undergoes cluster fission to yield [CoCl3]–; all acetylenic carboxylate complexes [CoCl(O2CR)2]– and [Co2Cl3(O2CR)2]– undergo decarboxylation. Isolation of the decarboxylated products followed by a second stage of CID results in a second decarboxylation event for all systems except for [CoCl(Me)(O2CMe)]–, which undergoes bond homolysis. In the final stage of CID, all acetylenic complexes undergo Glaser coupling, forming reduced Co anions. Overall dinuclear cobalt clusters are superior to mononuclear complexes at promoting decarboxylation and reductive coupling. The order of reactivity among the acetylide ligands is PhC≡C > MeC≡C > HC≡C.

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45

Ghosh, Sujit, Kinkar Biswas, Suchandra Bhattacharya, Pranab Ghosh, and Basudeb Basu. "Effect of the ortho-hydroxy group of salicylaldehyde in the A3 coupling reaction: A metal-catalyst-free synthesis of propargylamine." Beilstein Journal of Organic Chemistry 13 (March 16, 2017): 552–57. http://dx.doi.org/10.3762/bjoc.13.53.

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The synthesis of propargylamines via A3 coupling mostly under metal-catalyzed procedures is well known. This work invented an unprecedented effect of salicylaldehyde, one of the A3 coupling partners, which could lead to the formation of propargylamine, an important pharmaceutical building block, in the absence of any metal catalyst and under mild conditions. The role of the hydroxy group in ortho position of salicylaldehyde has been explored, which presumably activates the Csp–H bond of the terminal alkyne leading to the formation of propargylamines in good to excellent yields, thus negating the function of the metal catalyst. This observation is hitherto unknown, tested for a variety of salicylaldehyde, amine and acetylene, established as a general protocol, and is believed to be of interest for synthetic chemists from green chemistry.

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46

Caporale, Andrea, Stefano Tartaggia, Andrea Castellin, and Ottorino De Lucchi. "Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions." Beilstein Journal of Organic Chemistry 10 (February 12, 2014): 384–93. http://dx.doi.org/10.3762/bjoc.10.36.

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Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.

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47

Ueno, Atsushi, Jun Li, Constantin G. Daniliuc, Gerald Kehr, and Gerhard Erker. "Metal-Free Acetylene Coupling by the (C6 F5 )2 B−X 1,2-Halogenoboration Reaction." Chemistry - A European Journal 24, no. 40 (June 14, 2018): 10044–48. http://dx.doi.org/10.1002/chem.201802084.

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48

Shen, Zhaobing, Hong Zhao, Yue Liu, Zeyuan Kan, Ping Xing, Jinguang Zhong, and Biao Jiang. "Mercury-free nitrogen-doped activated carbon catalyst: an efficient catalyst for the catalytic coupling reaction of acetylene and ethylene dichloride to synthesize the vinyl chloride monomer." Reaction Chemistry & Engineering 3, no. 1 (2018): 34–40. http://dx.doi.org/10.1039/c7re00201g.

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49

Hocek, Michal, Hana Dvořáková, and Ivana Císařová. "Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages." Collection of Czechoslovak Chemical Communications 67, no. 10 (2002): 1560–78. http://dx.doi.org/10.1135/cccc20021560.

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Анотація:

The title 1,2-bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by hydrogenations. 6-[(1,3-Dimethyluracil-5-yl)ethynyl]purine (11) was prepared analogously and hydrogenated to the corresponding purine-pyrimidine conjugates linked via vinylene and ethylene linkers. Unlike the cytostatic bis(purin-6-yl)acetylenes and -diacetylenes, the purine-pyrimidine conjugates were inactive. Crystal structures of bis(purin-6-yl)acetylene 6a, -diacetylene 8a and -ethane 5a were determined by single-crystal X-ray diffraction.

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50

Toyota, Shinji. "Construction of novel molecular architectures from anthracene units and acetylene linkers." Pure and Applied Chemistry 84, no. 4 (February 9, 2012): 917–29. http://dx.doi.org/10.1351/pac-con-11-09-07.

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To create novel π-conjugated compounds, we constructed various molecular architectures from anthracene units and acetylene linkers. Several cyclic oligomers ranging from dimers to dodecamers were synthesized by macrocyclization of acyclic precursors with metal-catalyzed coupling reactions. The structures, dynamic behavior, and spectroscopic features were greatly influenced by the number of anthracene units and the combination of building units and linkers. Optically active and circular dichroism (CD)-active enantiomers of some chiral cyclic oligomers were resolved by chiral high-performance liquid chromatography (HPLC). Conformational analysis of hexamers and higher oligomers was performed with the aid of density functional theory (DFT) calculations. Acyclic oligomers underwent reversible folding–unfolding processes via photochemical and thermal reactions. These results suggest that transannular π–π interactions between anthracene units are important factors in controlling the structural and spectroscopic properties and functions of π-conjugated compounds. The scope and perspectives of this molecular design are discussed on the basis of previous studies.

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