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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Matsumura, Mio, Kaho Tsukada, Kiwa Sugimoto, Yuki Murata, and Shuji Yasuike. "Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes." Beilstein Journal of Organic Chemistry 18 (July 19, 2022): 863–71. http://dx.doi.org/10.3762/bjoc.18.87.

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Alkynyl selenides have attracted considerable research interest recently, owing to their applications in the biological and pharmaceutical fields. The Cu-catalyzed tandem reaction for the synthesis of novel alkynyl imidazopyridinyl selenides is presented. A one-pot synthesis route afforded alkynyl imidazopyridinyl selenides in moderate to good yields. This was achieved by a two-step reaction between terminal alkynes and diimidazopyridinyl diselenides, generated from imidazo[1,2-a]pyridines and Se powder, using 10 mol % of CuI and 1,10-phenanthroline as the catalytic system under aerobic conditions. The C(sp2)–Se and C(sp)–Se bond-formation reaction can be performed in one-pot by using inexpensive and easy to handle Se powder as the Se source. The reaction proceeded with terminal alkynes having various substitutions, such as aryl, vinyl, and alkyl groups. The obtained alkynyl imidazopyridinyl selenide was found to undergo nucleophilic substitution reaction on Se atom using organolithium reagents and 1,3-dipolar azide–alkyne cycloaddition based on the alkyne moiety.

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2

Sewald, Norbert, та Klaus Burger. "α-Trifluormethylsubstituierte α-Hydroxysäuren mit Alkinfunktionen in der Seitenkette / α-Trifluoromethyl Substituted α-Hydroxy Acids with Alkyne Functions in the Side Chain". Zeitschrift für Naturforschung B 45, № 6 (1 червня 1990): 871–75. http://dx.doi.org/10.1515/znb-1990-0619.

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Trifluoromethyl substituted α-hydroxy acids with alkyne functions in the side chain are obtained on reaction of trifluoro pyruvates with alkynyl Grignard reagents and alkali metal salts of alkynes, respectively.

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3

Heredia, Adrián A., and Alicia B. Peñéñory. "Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions." Beilstein Journal of Organic Chemistry 13 (May 16, 2017): 910–18. http://dx.doi.org/10.3762/bjoc.13.92.

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Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted acetylenes.

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4

Wu, Ge, Lin Min, Hongchen Li, Wenxia Gao, Jinchang Ding, Xiaobo Huang, Miaochang Liu, and Huayue Wu. "Metal-free synthesis of alkynyl alkyl selenides via three-component coupling of terminal alkynes, Se, and epoxides." Green Chemistry 20, no. 7 (2018): 1560–63. http://dx.doi.org/10.1039/c8gc00341f.

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Анотація:

A metal-free three-component coupling reaction of alkynes, Se powder and epoxides is described, providing an efficient, straightforward route for the preparation of alkynyl alkyl selenides via a double C–Se bond formation process.

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5

Reinus, Brandon, and Sean Kerwin. "Preparation and Utility of N-Alkynyl Azoles in Synthesis." Molecules 24, no. 3 (January 24, 2019): 422. http://dx.doi.org/10.3390/molecules24030422.

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Анотація:

Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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6

Li, Qingjiang, Jiatong Guo, and Zhongwu Guo. "Direct access to various C3-substituted sialyl glycal derivatives from 3-iodo-sialyl glycals." Organic & Biomolecular Chemistry 19, no. 46 (2021): 10169–73. http://dx.doi.org/10.1039/d1ob01977e.

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Sialyl glycal C3-aryl, alkyl, alkenyl, and alkynyl derivatives useful for sialylidase inhibitor discovery were efficiently synthesized by a new method based on the cross-coupling of 3-iodo-sialyl glycal with boronic acids, alkenes, and alkynes.

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7

Jover, Jesús. "Copper-Catalyzed Eglinton Oxidative Homocoupling of Terminal Alkynes: A Computational Study." Journal of Chemistry 2015 (2015): 1–8. http://dx.doi.org/10.1155/2015/430358.

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The copper(II) acetate mediated oxidative homocoupling of terminal alkynes, namely, the Eglinton coupling, has been studied with DFT methods. The mechanism of the whole reaction has been modeled using phenylacetylene as substrate. The obtained results indicate that, in contrast to some classical proposals, the reaction does not involve the formation of free alkynyl radicals and proceeds by the dimerization of copper(II) alkynyl complexes followed by a bimetallic reductive elimination. The calculations demonstrate that the rate limiting-step of the reaction is the alkyne deprotonation and that more acidic substrates provide faster reactions, in agreement with the experimental observations.

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8

Frontier, Alison J., Shukree Abdul-Rashed, and Connor Holt. "Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications." Synthesis 52, no. 14 (April 9, 2020): 1991–2007. http://dx.doi.org/10.1055/s-0039-1690869.

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Анотація:

This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo- addition-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

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9

Sun, Fenggang, Miao Li, and Zhenhua Gu. "Pd/norbornene-catalyzed sequential ortho-C–H alkylation and ipso-alkynylation: a 1,1-dimethyl-2-alkynol strategy." Organic Chemistry Frontiers 3, no. 3 (2016): 309–13. http://dx.doi.org/10.1039/c5qo00391a.

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A palladium/norbornene-catalyzedortho-C–H alkylation andipso-alkynylation reaction for the synthesis of 2-alkyl-1-alkynyl arenes was reported, where the use of bulky 1,1-dimethyl-2-alkynols led to significant suppression of the formation ofO-alkylation and norbornene alkynylation by-products.

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10

Chowdhury, Roomi Mohima, and Jonathan D. Wilden. "An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre." Organic & Biomolecular Chemistry 13, no. 21 (2015): 5859–61. http://dx.doi.org/10.1039/c5ob00494b.

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Анотація:

A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N′-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.

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11

Banks, Surya R., Kyung Min Yoo, and Mark E. Welker. "Synthesis of Polar Aromatic Substituted Terminal Alkynes from Propargyl Amine." Molbank 2021, no. 2 (April 25, 2021): M1206. http://dx.doi.org/10.3390/m1206.

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Анотація:

A series of small molecules containing polar aromatic substituents and alkynes have been synthesized. One–pot preparations of polar aromatic molecules containing an alkynyl imine and alkynyl amide are reported. A one-pot preparation of a catechol containing an alkynyl amine was also attempted but in our hands it proved much better to synthesize this target molecule via a three step synthesis which we also report here.

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12

Fukumoto, Yoshiya, Masato Daijo, and Naoto Chatani. "Rhenium(I)-catalyzed reaction of terminal alkynes with imines leading to allylamine derivatives." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 283–89. http://dx.doi.org/10.1515/pac-2014-5003.

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Abstract The rhenium-catalyzed reaction of terminal alkynes with imines gives N-alkylideneallylamine derivatives. A diphenylmethyl group as the substituent on the imine nitrogen gave the best result. Deuterium labeling experiments revealed that the regioselective addition of both the hydrogen and the N-alkylideneaminoalkyl group to the terminal alkynes also proceeded stereoselectively. While alkynes bearing primary and secondary alkyl-, vinyl-, and aryl groups were applicable to the catalytic reaction, tertiary alkyl- and silyl-substituted alkynes gave propargylamines. The C–C bond-forming step via the nucleophilic attack of the alkynyl β-carbon on the imine carbon leading to the formation of a vinylidene rhenium species appears to be involved in the catalytic cycle.

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13

Gong, Xinxing, Min Yang, Jin-Biao Liu, Fu-Sheng He, Xiaona Fan, and Jie Wu. "A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide." Green Chemistry 22, no. 6 (2020): 1906–10. http://dx.doi.org/10.1039/d0gc00332h.

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A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

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14

Jin, Shengnan, Fan Chen, Pengcheng Qian, and Jiang Cheng. "Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration." Organic & Biomolecular Chemistry 19, no. 11 (2021): 2416–19. http://dx.doi.org/10.1039/d1ob00192b.

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A di-tert-butyl peroxide (DTBP)-promoted difunctionalization of α-aryl α-alkynyl allylic alcohols with alkyl nitriles was developed, affording a series of α-alkynyl γ-cyano functionalized ketones in moderate yields.

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15

Böser, Richard, Lars Denker, and René Frank. "N-Heterocyclic Carbene Adducts of Alkynyl Functionalized 1,3,2-Dithioborolanes." Molecules 24, no. 9 (April 30, 2019): 1690. http://dx.doi.org/10.3390/molecules24091690.

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Alkynyl functionalized boron compounds are versatile intermediates in the areas of medicinal chemistry, materials science, and optical materials. In particular, alkynyl boronate esters [R1−C≡C−B(OR2)2] are of interest since they provide reactivity at both the alkyne entity, with retention of the B−C bond or alkyne transfer to electrophilic substrates with scission of the latter. The boron atom is commonly well stabilized due to (i) the extraordinary strength of two B−O bonds, and (ii) the chelate effect exerted by a bifunctional alcohol. We reasoned that the replacement of a B−O for a B−S bond would lead to higher reactivity and post-functionalization in the resulting alkynyl boronate thioesters [R1−C≡C−B(S2X)]. Access to this poorly investigated class of compounds starts form chloro dithioborolane cyclo-Cl−B(S2C2H4) as a representative example. Whereas syntheses of three coordinate alkynyl boronate thioesters [R1−C≡C−B(S2X)] proved to be ineffective, the reactions of NHC-adducts (NHC = N-heterocyclic carbene) of cyclo-Cl-B(S2C2H4) afforded the alkyne substituted thioboronate esters in good yield. The products NHC−B(S2C2H4)(C≡C-R1) are remarkably stable towards water and air, which suggests their use as boron-based building blocks for applications akin to oxygen-based boronate esters.

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16

Yam, Chi Ming, Adam Dickie, Aramice Malkhasian, Ashok K. Kakkar, and M. A. Whitehead. "Article." Canadian Journal of Chemistry 76, no. 11 (November 1, 1998): 1766–78. http://dx.doi.org/10.1139/v98-151.

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The hydrolysis of surface-bound basic tin-amide moieties with acidic protons of alkynyl chromophores leads to molecular self-assembly of a variety of rigid-rod alkynes on inorganic oxide surfaces such as glass, quartz, and single crystal silicon. Characterization of these newly developed thin films was achieved by contact-angle goniometry, FTIR-ATR, ellipsometry, and X-ray photoelectron spectroscopy, which indicate that these thin films are densely packed. Comparative molecular mechanics modeling studies on unbound and chemisorbed -Sn-Ctriple bondC-H monomer, dimer, trimer, and a 12 × 12 (144 molecule) model substrate, suggest that surface anchoring of Sn-alkynyl units is essential for highly ordered thin-film structures that can effect topochemical polymerization. Preliminary MO calculations on a 4 × 4 model show conjugated molecular orbitals through the system.Key words: molecular self-assembly, rigid-rod alkynes, acid-base hydrolysis, tin-alkynyl thin films, molecular mechanics modeling studies, topochemical polymerization, molecular orbitals.

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17

He, Haiqing, and Hong-Bo Qin. "ZnBr2-catalyzed directC-glycosylation of glycosyl acetates with terminal alkynes." Organic Chemistry Frontiers 5, no. 12 (2018): 1962–66. http://dx.doi.org/10.1039/c8qo00380g.

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18

Chronopoulos, Demetrios D., Miroslav Medved’, Piotr Błoński, Zdeněk Nováček, Petr Jakubec, Ondřej Tomanec, Aristides Bakandritsos, Veronika Novotná, Radek Zbořil, and Michal Otyepka. "Alkynylation of graphene via the Sonogashira C–C cross-coupling reaction on fluorographene." Chemical Communications 55, no. 8 (2019): 1088–91. http://dx.doi.org/10.1039/c8cc08492k.

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19

Wang, Yuguang, Yi You, and Zhiqiang Weng. "Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes." Organic Chemistry Frontiers 2, no. 5 (2015): 574–77. http://dx.doi.org/10.1039/c5qo00045a.

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20

Schäfer, Martin, Justin Wolf, and Helmut Werner. "Binding Two C2Units to an Electron-Rich Transition-Metal Center: The Interplay of Alkyne(alkynyl), Bisalkynyl(hydrido), Alkynyl(vinylidene), Alkynyl(allene), Alkynyl(olefin), and Alkynyl(enyne) Rhodium Complexes†." Organometallics 23, no. 24 (November 2004): 5713–28. http://dx.doi.org/10.1021/om049389f.

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21

Cao, Wenxuan, Sheng-Li Niu, Li Shuai, and Qing Xiao. "Copper-catalysed three-component carboiodination of arynes: expeditious synthesis of o-alkynyl aryl iodides." Chemical Communications 56, no. 6 (2020): 972–75. http://dx.doi.org/10.1039/c9cc09160b.

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22

Kehr, Gerald, and Gerhard Erker. "Advanced 1,1-carboboration reactions with pentafluorophenylboranes." Chemical Science 7, no. 1 (2016): 56–65. http://dx.doi.org/10.1039/c5sc03282b.

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23

Ma, Jing-Jing, and Wen-Bin Yi. "Copper-catalyzed fluoroalkylation of alkynes, and alkynyl & vinyl carboxylic acids with fluoroalkyl halides." Organic & Biomolecular Chemistry 15, no. 20 (2017): 4295–99. http://dx.doi.org/10.1039/c7ob00641a.

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24

Zhu, Chuan, Chao Feng, and Motoki Yamane. "Pd/Cu cooperative catalysis: an efficient synthesis of (3-isoindazolyl)allenes via cross-coupling of 2-alkynyl azobenzenes and terminal alkynes." Chemical Communications 53, no. 17 (2017): 2606–9. http://dx.doi.org/10.1039/c7cc00562h.

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25

Petko, Dina, Samuel Koh, and William Tam. "Transition Metal-Catalyzed Reactions of Alkynyl Halides." Current Organic Synthesis 16, no. 4 (July 4, 2019): 546–82. http://dx.doi.org/10.2174/1570179416666190329200616.

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Анотація:

Background: Transition metal-catalyzed reactions of alkynyl halides are a versatile means of synthesizing a wide array of products. Their use is of particular interest in cycloaddition reactions and in constructing new carbon-carbon and carbon-heteroatom bonds. Transition metal-catalyzed reactions of alkynyl halides have successfully been used in [4+2], [2+2], [2+2+2] and [3+2] cycloaddition reactions. Many carbon-carbon coupling reactions take advantage of metal-catalyzed reactions of alkynyl halides, including Cadiot-Chodkiewicz, Suzuki-Miyaura, Stille, Kumada-Corriu and Inverse Sonogashira reactions. All the methods of constructing carbon-nitrogen, carbon-oxygen, carbon-phosphorus, carbon-sulfur, carbon-silicon, carbon-selenium and carbon-tellurium bonds employed alkynyl halides. Objective: The purpose of this review is to highlight and summarize research conducted in transition metalcatalyzed reactions of alkynyl halides in recent years. The focus will be placed on cycloaddition and coupling reactions, and their scope and applicability to the synthesis of biologically important and industrially relevant compounds will be discussed. Conclusion: It can be seen from the review that the work done on this topic has employed the use of many different transition metal catalysts to perform various cycloadditions, cyclizations, and couplings using alkynyl halides. The reactions involving alkynyl halides were efficient in generating both carbon-carbon and carbonheteroatom bonds. Proposed mechanisms were included to support the understanding of such reactions. Many of these reactions face retention of the halide moiety, allowing additional functionalization of the products, with some new products being inaccessible using their standard alkyne counterparts.

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26

Hu, Lingfei, Han Gao, Yanlei Hu, Xiangying Lv, Yan-Bo Wu, and Gang Lu. "Origins of regio- and stereoselectivity in Cu-catalyzed alkyne difunctionalization with CO₂ and organoboranes." Organic Chemistry Frontiers 9, no. 4 (2022): 1033–39. http://dx.doi.org/10.1039/d1qo01788h.

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27

Peng, Lifen, Zhifang Hu, Hong Wang, Li Wu, Yinchun Jiao, Zilong Tang, and Xinhua Xu. "Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes." RSC Advances 10, no. 17 (2020): 10232–44. http://dx.doi.org/10.1039/d0ra01286f.

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Cyanation of alkynes was highlighted. Direct cyanation and hydrocyanation gave alkynyl cyanides and alkenyl nitriles. Dicyanation produced 1,2-dicyano adducts. Cyanofunctionalization afforded functional cyano compounds.

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28

Jin, Weiwei, Mingchang Wu, Zhimin Xiong, and Gangguo Zhu. "Visible-light induced three-component alkynyl-difluoroalkylation of unactivated alkenes." Chemical Communications 54, no. 57 (2018): 7924–27. http://dx.doi.org/10.1039/c8cc03105c.

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29

Meesin, Jatuporn, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Pawaret Leowanawat, and Chutima Kuhakarn. "Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3662–69. http://dx.doi.org/10.1039/c7ob00366h.

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30

Schumacher, Ricardo F., Benhur Godoi, Carla K. Jurinic, and Andrei L. Belladona. "Diorganyl Dichalcogenides and Copper/Iron Salts: Versatile Cyclization System To Achieve Carbo- and Heterocycles from Alkynes." Synthesis 53, no. 15 (March 24, 2021): 2545–58. http://dx.doi.org/10.1055/a-1463-4098.

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Анотація:

AbstractOrganochalcogen-containing cyclic molecules have shown several promising pharmacological properties. Consequently, different strategies have been developed for their synthesis in the past few years. Particularly due to the low cost and environmental aspects, copper- and iron-promoted cyclization reactions of alkynyl substrates have been broadly and efficiently applied for this purpose. This short review presents an overview of the most recent advances in the synthesis of organochalcogen-containing carbo- and heterocycles by reacting diorganyl disulfides, diselenides, and ditellurides with alkyne derivatives in the presence of copper and iron salts to promote cyclization reactions.1 Introduction2 Synthesis of Carbo- and Heterocycles via Reactions of Alkynes with Diorganyl Dichalcogenides and Copper Salts3 Synthesis of Carbo- and Heterocycles via Reactions of Alkynes with Diorganyl Dichalcogenides and Iron Salts4 Conclusions

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31

Reddy, C. Bal, Richa Bharti, Sandeep Kumar, and Pralay Das. "Supported palladium nanoparticles-catalyzed decarboxylative coupling approaches to aryl alkynes, indoles and pyrrolines synthesis." RSC Advances 6, no. 75 (2016): 71117–21. http://dx.doi.org/10.1039/c6ra12046f.

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The polystyrene supported palladium (Pd@PS) nanoparticles catalyzed decarboxylative coupling of arylhalides and alkynyl carboxylic acids was developed for the synthesis of diaryl alkynes, indoles and pyrrolines.

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32

Song, Zhi-Yong, Chun-Lin Zhang, and Song Ye. "Visible light promoted coupling of alkynyl bromides and Hantzsch esters for the synthesis of internal alkynes." Organic & Biomolecular Chemistry 17, no. 1 (2019): 181–85. http://dx.doi.org/10.1039/c8ob02912a.

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33

Wu, Zhilian, Lei Sun, Qinggang Liu, Xiaofeng Yang, Xue Ye, Yancheng Hu, and Yanqiang Huang. "A Schiff base-modified silver catalyst for efficient fixation of CO2 as carboxylic acid at ambient pressure." Green Chemistry 19, no. 9 (2017): 2080–85. http://dx.doi.org/10.1039/c7gc00923b.

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34

Amarasiri, Madushani, Yen Vo, Michael G. Gardiner, Perlita Poh, Priscilla Soo, Megan Pavy, Nadine Hein, et al. "The Synthesis and Biological Evaluation of Some C-9 and C-10 Substituted Derivatives of the RNA Polymerase I Transcription Inhibitor CX-5461." Australian Journal of Chemistry 74, no. 7 (2021): 540. http://dx.doi.org/10.1071/ch21049.

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Анотація:

The regio-isomeric alkynyl-substituted derivatives, 2 and 3, of the RNA Polymerase I (Pol I) transcription inhibitor CX-5461 (1) were prepared and the active one (compound 3) subjected to click reactions ([3+2]-cycloaddition reactions) with certain alkyl azides bearing biotin or fluorescent tags. Compounds 2 and 3, as well as four [3+2]-cycloadducts of the latter, were subjected to biological evaluation in a human acute myeloid leukemia cell line model. Among the six compounds tested only alkyne 3 remained active but this was less potent than parent 1.

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35

Zhang, Bo, Hongmei Qu, Zhongxuan Li, Yuanyuan Zhai, Xiaolu Zhou, and Liqiang Liu. "Zirconocene-mediated selective synthesis of 1,4-bis(alkynyl)benzenes." Journal of Chemical Research 44, no. 9-10 (March 24, 2020): 571–75. http://dx.doi.org/10.1177/1747519820912675.

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Анотація:

A series of novel 1,4-bis(alkynyl)benzene derivatives were synthesized from trimethylsilyl-substituted alkynes by the mediation of zirconocene with excellent regioselectivity in high yields. The 3,6-bis(trimethylsilyl)-4,5-dialkylphthalic acid dimethyl esters were prepared by cycloaddition of 2,5-bis(trimethylsilyl)zirconacyclopentadienes to dimethyl acetylenedicarboxylate. After iodination with iodine monochloride, 3,6-diiodo-4,5-dialkylphthalic acid dimethyl esters reacted with terminal alkynes to prepare the corresponding 1,4-bis(alkynyl)benzene derivatives by Sonogashira coupling reactions. After removal of trimethylsilyl, 4,5-dibutyl-3,6-bis(ethynyl)phthalic acid dimethyl ester (compound 3) reacted with 4-iodobenzoic acid ethyl ester and 2-iodothiophene, respectively, to obtain the corresponding products 4a and 4c. Compound 3 can be extended to higher oligomers, which reacted with 1-bromo-4-iodobenzene and phenylacetylene in a stepwise manner under Sonogashira conditions to give the phenylene-ethynylene oligomer 5 in an isolated yield of 85%. The structures of the products were confirmed by 1H NMR spectroscopy, 13C NMR spectroscopy, and MS. The optical properties of the 1,4-bis(alkynyl)benzene derivatives were studied by UV-Vis spectroscopy and fluorescence spectra. The results indicated that some can be developed into potential photovoltaic materials.

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36

Iqbal, Naila, Naeem Iqbal, Sung Su Han, and Eun Jin Cho. "Synthesis of fluoroalkylated alkynes via visible-light photocatalysis." Organic & Biomolecular Chemistry 17, no. 7 (2019): 1758–62. http://dx.doi.org/10.1039/c8ob02486c.

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Анотація:

Fluoroalkylated alkynes, which are versatile building blocks for the synthesis of various biologically active organofluorine compounds, were synthesized from easily available alkynyl halides and fluoroalkyl halides by visible-light photocatalysis.

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37

Dastjerdi, Hossein Fasihi, Manijeh Nematpour, Elham Rezaee, Mehdi Jahani, and Sayyed Abbas Tabatabai. "A Novel Copper-Catalyzed Synthesis of N-Monosubstituted 2-Alkynimidamides from 1-Alkynes and Trichloroacetamidines." Letters in Organic Chemistry 17, no. 9 (September 17, 2020): 704–8. http://dx.doi.org/10.2174/1570178616666191023142821.

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Анотація:

A one-pot Cu-catalyzed synthesis of functionalized alkynyl imidamide by terminal alkynes, trichloroacetonitrile and aniline or benzyl amine is reported. The compounds were produced via coupling reaction of terminal alkynes with trichloroacetamidine. This method was performed under mild, ligand-free conditions and easy work-up method.

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38

Bellina, Fabio, Matteo Biagetti, Sara Guariento, Marco Lessi, Mattia Fausti, Paolo Ronchi, and Elisabetta Rosadoni. "Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives." RSC Advances 11, no. 41 (2021): 25504–9. http://dx.doi.org/10.1039/d1ra05303e.

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Анотація:

The regioselective synthesis of 2-alkynyl(benz)imidazoles was successfully achieved by Pd(ii)/Ag(i)-mediated dehydrogenative alkynylation of the corresponding (benz)imidazoles with terminal alkynes in an open vessel.

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39

Radhika, Sankaran, Nissy Ann Harry, Mohan Neetha, and Gopinathan Anilkumar. "Recent trends and applications of the Cadiot–Chodkiewicz reaction." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9081–94. http://dx.doi.org/10.1039/c9ob01757g.

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40

Wang, Yan, Xiaolong Yang, and Jianqiang Yu. "A polysalen based on polyacylamide stabilized palladium nanoparticle catalyst for efficient carbonylative Sonogashira reaction in aqueous media." RSC Advances 7, no. 51 (2017): 31850–57. http://dx.doi.org/10.1039/c7ra04910b.

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Анотація:

Pd nanoparticles immobilized on polysalen based on polyacylamide was synthesized and used for carbonylative Sonogashira coupling of aryl iodides with terminal alkynes to produce α,β-alkynyl ketones in aqueous media.

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41

Wang, Cheng, Christopher Flinn, and Yuming Zhao. "Intramolecular alkyne–dithiolium cycloaddition: a joint experimental and DFT mechanistic study." RSC Advances 7, no. 58 (2017): 36623–31. http://dx.doi.org/10.1039/c7ra05087a.

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42

Shen, Kun, Xiuling Han, Guoqin Xia, and Xiyan Lu. "Cationic Pd(ii)-catalyzed cyclization of N-tosyl-aniline tethered alkynyl ketones initiated by hydropalladation of alkynes: a facile way to 1,2-dihydro or 1,2,3,4-tetrahydroquinoline derivatives." Organic Chemistry Frontiers 2, no. 2 (2015): 145–49. http://dx.doi.org/10.1039/c4qo00286e.

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Анотація:

A cationic Pd(ii)-catalyzed intramolecular alkyne-carbonyl reductive coupling reaction of N-tosyl-aniline tethered alkynyl ketones under transfer hydrogenation conditions to give hydroquinolines is developed.

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43

Davenel, Vincent, Chloé Puteaux, Christian Nisole, Fabien Fontaine-Vive, Jean-Marie Fourquez, and Véronique Michelet. "Indium-Catalyzed Cycloisomerization of 1,6-Cyclohexenylalkynes." Catalysts 11, no. 5 (April 24, 2021): 546. http://dx.doi.org/10.3390/catal11050546.

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Анотація:

Efficient four- and five-step routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes has been developed. This atom-economical catalytic process was optimized and relied on the efficiency of InCl3 leading to the preparation of functionalized bicyclic adducts in up to 99% isolated yield. The cyclization occurred on two different processes (5-exo versus 6-endo pathway) and were influenced by the substitution of the alkynyl moiety. The exo process was favored for non-substituted alkynes whereas the endo pathway was generally observed for substituted alkynes. Then, the presence of electron-withdrawing groups on the aryl substituted alkyne increased the ratio of the exo isomer. DFT calculations were performed on stability of intermediates and corroborated the intervention of InCl3.

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44

Chang, Sheng, Ying Liu, Shu Zhu Yin, Lin Lin Dong, and Jian Feng Wang. "Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process." New Journal of Chemistry 43, no. 14 (2019): 5357–62. http://dx.doi.org/10.1039/c8nj02964d.

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Анотація:

The decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions.

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45

Duran-Sampedro, Gonzalo, Eduardo Palao, Antonia R. Agarrabeitia, Santiago de la Moya, Noël Boens, and María J. Ortiz. "Negishi reaction in BODIPY dyes. Unprecedented alkylation by palladium-catalyzed C–C coupling in boron dipyrromethene derivatives." RSC Adv. 4, no. 37 (2014): 19210–13. http://dx.doi.org/10.1039/c4ra00651h.

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46

Mukherjee, Nirmalya, Debasish Kundu, and Brindaban C. Ranu. "A co-operative Ni–Cu system for Csp–Csp and Csp–Csp2 cross-coupling providing a direct access to unsymmetrical 1,3-diynes and en-ynes." Chem. Commun. 50, no. 99 (2014): 15784–87. http://dx.doi.org/10.1039/c4cc07413k.

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Анотація:

An efficient cross coupling of alkynes with alkynyl and alkenyl halides catalysed by a Ni–Cu system without any ligand leading to the synthesis of a series of functionalised 1,3-di-ynes and en-ynes has been achieved.

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47

Cámara, Jéssica, M. Carmen Blanco, Antonio Laguna, Panče Naumov, and M. Concepción Gimeno. "A stable gold(i)–enyne species obtained by alkyne carboauration in a complex rearrangement." Chemical Communications 53, no. 66 (2017): 9202–5. http://dx.doi.org/10.1039/c7cc03713a.

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Анотація:

An unprecedented tetranuclear gold derivative with unusual gold–enyne moieties is prepared by a mild and neat rearrangement of a dinuclear gold complex with a bridging bis(diphenylphosphino)alkyne and terminal alkynyl ligands.

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48

Mukherjee, Nirmalya, Subhajit Pal, Amit Saha, and Brindaban C. Ranu. "Silver-catalyzed carbon–selenium cross-coupling using N-(phenylseleno)phthalimide: an alternate approach to the synthesis of organoselenides." Canadian Journal of Chemistry 95, no. 1 (January 2017): 51–56. http://dx.doi.org/10.1139/cjc-2016-0427.

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Анотація:

Silver(I) catalyzed phenylselenylation of terminal alkynes and organoboronic acids has been demonstrated using N-(phenylseleno)phthalimide as an electrophilic SePh donor. A wide variety of terminal alkynes and organoboronic acids are selenylated efficiently to produce the corresponding alkynyl and diaryl selenides, respectively, in good yields. Silver(I) acts as a Lewis acid in this process.

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49

Tan, Jin-Fay, Carl Thomas Bormann, Kay Severin, and Nicolai Cramer. "Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes." Chemical Science 13, no. 12 (2022): 3409–15. http://dx.doi.org/10.1039/d2sc00294a.

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Анотація:

Three mild and operationally simple fluorination protocols convert 1-alkynyl triazenes either into attractive 1,1,2,2-tetrafluoro alkyl triazenes, α-difluoro α-triazenyl ketones or α-difluoro acyl triazenes.

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50

Galadzhun, Iurii, Rafal Kulmaczewski, Namrah Shahid, Oscar Cespedes, Mark J. Howard, and Malcolm A. Halcrow. "The flexibility of long chain substituents influences spin-crossover in isomorphous lipid bilayer crystals." Chemical Communications 57, no. 33 (2021): 4039–42. http://dx.doi.org/10.1039/d1cc01073e.

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