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1

Wang, Lei, Jincan Yan, Pinhua Li, Min Wang, and Caina Su. "The effects of amines on oxidative homo-coupling of terminal alkynes promoted by copper salts." Journal of Chemical Research 2005, no. 2 (2005): 112–15. http://dx.doi.org/10.3184/0308234054497083.

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The effects of all kinds of amines on homo-couplings (Glaser reactions) of terminal alkynes promoted by copper salts and the Sonogashira coupling reactions were studied systematically. Diethylamine (2° amine) can serve as an excellent solvent, base and coordination ligand in the oxidative homo-coupling of terminal alkynes and several modified Glaser coupling procedures have been developed which are based on a catalytic amount of cuprous salts (CuI, CuBr or CuCl) with diethylamine systems. Homo-coupling of terminal acetylenes in the Sonogashira reaction could be inhibited by using triethylamine
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2

Sinai, Ádám, Ádám Mészáros, Ádám Balogh, Márton Zwillinger, and Zoltán Novák. "Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction." Synthesis 49, no. 11 (2017): 2374–88. http://dx.doi.org/10.1055/s-0036-1588981.

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Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot Sonogashira–Sonogashira­ and Sonogashira–CuAAC reactions.
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3

Albano, Gianluigi, and Laura Antonella Aronica. "Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds." Catalysts 10, no. 1 (2019): 25. http://dx.doi.org/10.3390/catal10010025.

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The acyl Sonogashira reaction represents an extension of Sonogashira cross-coupling to acid chlorides which replace aryl or vinyl halides, while terminal acetylenes are used as coupling partners in both reactions. The introduction of a carbonyl functional group on the alkyne backbone determines a radical change in the reactivity of the products. Indeed, α,β-alkynyl ketones can be easily converted into different heterocyclic compounds depending on the experimental conditions employed. Due to its potential, the acyl Sonogashira reaction has been deeply studied with particular attention to the na
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4

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety
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5

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550/jcsp/43.01.2021.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety
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6

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000009.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety
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7

Nakamura, Keiichi, Hitoshi Okubo, and Masahiko Yamaguchi. "Low Temperature Sonogashira Coupling Reaction." Synlett 1999, no. 5 (1999): 549–50. http://dx.doi.org/10.1055/s-1999-2684.

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8

Ji, Yuan, Ning Zhong, Zinan Kang, Guobing Yan, and Ming Zhao. "Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes." Synlett 29, no. 02 (2017): 209–14. http://dx.doi.org/10.1055/s-0036-1590907.

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Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction
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9

Steven, Alan. "Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates." Synthesis 51, no. 13 (2019): 2632–47. http://dx.doi.org/10.1055/s-0037-1610714.

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Micellar reaction conditions, in a predominantly aqueous medium, have been developed for transformations commonly used by synthetic chemists working in the pharmaceutical industry to discover and develop drug candidates. The reactions covered in this review are the Suzuki–Miyaura, Miyaura borylation, Sonogashira coupling, transition-metal-catalysed CAr–N coupling, SNAr, amidation, and nitro reduction. Pharmaceutically relevant examples of these applications will be used to show how micellar conditions can offer advantages in yield, operational ease, amount of waste generated, transition-metal
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10

Hrizi, Asma, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, and Jérôme Thibonnet. "Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions." Molecules 26, no. 17 (2021): 5287. http://dx.doi.org/10.3390/molecules26175287.

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An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.
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11

Gottardo, Christine, Thomas M. Kraft, M. Selim Hossain, Peter V. Zawada, and Heidi M. Muchall. "Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction." Canadian Journal of Chemistry 86, no. 5 (2008): 410–15. http://dx.doi.org/10.1139/v08-038.

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Relative rate constants (krel) for the Sonogashira coupling were determined in competitive reactions between iodobenzene and a series of para- and meta-substituted iodobenzenes and compared to the charge on iodine and the z-component of the quadrupole moment of the iodine-bearing carbon. We use an Hammett correlation analysis and the computational data to provide further evidence that the rate limiting step of the Sonogashira reaction is the initial oxidative addition of Pd to the carbon-iodine bond.Key words: Sonogashira, competitive reactions, Hammett correlation.
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12

Patonay, Tamás, István Pazurik, and Anita Ábrahám. "C-Alkynylation of Chromones by Sonogashira Reaction." Australian Journal of Chemistry 66, no. 6 (2013): 646. http://dx.doi.org/10.1071/ch13006.

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Sonogashira reaction of bromochromones and -flavones with a bromine atom on their benzene or heterocyclic ring with various terminal alkynes gave the desired products with nearly the same efficiency as the previously used iodine derivatives. The coupling reactions were performed in the presence of [tetrakis(triphenylphosphine)palladium(0)], copper(i) co-catalyst, and triethylamine, resulting in the formation of numerous hitherto unknown alkynylated oxygen heterocycles, and provide further proof for the applicability of this reaction for these O-heterocycles. Chromones with ethynyl functionalit
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13

Kanwal, Iram, Aqsa Mujahid, Nasir Rasool, et al. "Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review." Catalysts 10, no. 4 (2020): 443. http://dx.doi.org/10.3390/catal10040443.

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Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and r
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14

Elangovan, Arumugasamy, Yu-Hsiang Wang, and Tong-Ing Ho. "Sonogashira Coupling Reaction with Diminished Homocoupling." Organic Letters 5, no. 11 (2003): 1841–44. http://dx.doi.org/10.1021/ol034320+.

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15

Zhai, Hongbin, Zhaolong Tong, Peng Gao, Haibing Deng, Lei Zhang, and Peng-Fei Xu. "Propylene Oxide Assisted Sonogashira Coupling Reaction." Synlett 2008, no. 20 (2008): 3239–41. http://dx.doi.org/10.1055/s-0028-1087368.

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16

Venkata Krishna Reddy, Motakatla, Peddiahgari Vasu Govardhana Reddy, and Cirandur Suresh Reddy. "PEPPSI-SONO-SP2: a new highly efficient ligand-free catalyst system for the synthesis of tri-substituted triazine derivatives via Suzuki–Miyaura and Sonogashira coupling reactions under a green approach." New Journal of Chemistry 40, no. 6 (2016): 5135–42. http://dx.doi.org/10.1039/c5nj03299g.

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17

Murata, Yuki, Yuya Nishi, Mio Matsumura, and Shuji Yasuike. "Palladium-Catalyzed Cross-Coupling Reaction of Bis(cyclopentadienyl)diaryltitaniums with Terminal Alkynes." Reactions 4, no. 4 (2023): 657–66. http://dx.doi.org/10.3390/reactions4040037.

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Organotitanium compounds find application in diverse reactions, including carbon–carbon bond formation and oxidation. While titanium (IV) compounds have been used in various applications, the potential of bis(cyclopentadienyl)diaryltitanium in cross-coupling reactions remains unexplored. This study focuses on Sonogashira-type cross-coupling reactions involving terminal alkynes and organotitanium compounds. Diaryltitanocenes were synthesized using titanocene dichloride with lithium intermediates derived from aryl iodide. Under open-flask conditions, reactions of diphenyltitanocenes with ethynyl
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18

Chowdhury, Pritam Roy, Debabrata Singha, Sudeshna Sawoo, Manas Ghosh, and Nilasish Pal. "Sonogashira Coupling Reaction and its Application in Dendrimer Synthesis." Asian Journal of Chemistry 34, no. 8 (2022): 1939–57. http://dx.doi.org/10.14233/ajchem.2022.23748.

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Sonogashira cross-coupling process is a synthetic method for producing aryl-alkyne conjugates. In last few years, several researchers have been able to explore the divergent and convergent approaches of dendrimer synthesis. Dendrimers are radially symmetrical molecules which are nanoscale in size and have a well-defined homogeneous and monodisperse structure with symmetric or asymmetric core, inner shell and outer shell. Several dendrimers have been produced via various C-C coupling processes. In present review, we focused on the synthesis of few dendrimers using the Sonogashira Coupling react
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19

Shen, Hongyun, Chao Shen, Chao Chen, Anming Wang, and Pengfei Zhang. "Novel glycosyl pyridyl-triazole@palladium nanoparticles: efficient and recoverable catalysts for C–C cross-coupling reactions." Catalysis Science & Technology 5, no. 4 (2015): 2065–71. http://dx.doi.org/10.1039/c5cy00013k.

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20

Murashkina, A. V., A. Yu Mitrofanov, and I. P. Beletskaya. "Copper in Cross-Coupling Reactions: I. Sonogashira-Hagihara Reaction." Russian Journal of Organic Chemistry 55, no. 10 (2019): 1445–58. http://dx.doi.org/10.1134/s1070428019100014.

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21

Puechmongkol, Suttikiat, Boonchoat Paosawatyanyong, and Worawan Bhanthumnavin. "Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds." Materials Science Forum 695 (July 2011): 113–16. http://dx.doi.org/10.4028/www.scientific.net/msf.695.113.

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An efficient Sonogashira-type coupling reaction of terminal alkynes and aryl bromides by microwave activation with short reaction time under mild conditions are presented. It is illustrated herein that the traditional Sonogashira coupling reaction can be achieved with a much more efficient yet environmentally friendly condition. In contrary to the usually required 10 mol% Pd loading and the use of conventional heating at 60 °C for 24 h in order for a reaction to proceed satisfactorily, with a 100 W microwave activation, the reaction of terminal alkynes with substituted aryl bromides can be ach
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22

Mohajer, Fatemeh, Majid M. Heravi, Vahideh Zadsirjan, and Nargess Poormohammad. "Copper-free Sonogashira cross-coupling reactions: an overview." RSC Advances 11, no. 12 (2021): 6885–925. http://dx.doi.org/10.1039/d0ra10575a.

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23

Lee, Sunwoo, and Muhammad Aliyu Idris. "Recent Advances in Decarboxylative Reactions of Alkynoic Acids." Synthesis 52, no. 16 (2020): 2277–98. http://dx.doi.org/10.1055/s-0040-1707600.

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Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogena
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24

Stolle, Achim, and Bernd Ondruschka. "Solvent-free reactions of alkynes in ball mills: It is definitely more than mixing." Pure and Applied Chemistry 83, no. 7 (2011): 1343–49. http://dx.doi.org/10.1351/pac-con-10-09-26.

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This contribution presents two solvent-free reactions of terminal alkynes in ball mills: Pd-catalyzed Sonogashira cross-coupling and Cu-catalyzed homo-coupling (Glaser reaction). The results are compared to other solvent-free reaction protocols, which have been published up to date for those types of reactions. Reactions are assessed on the basis of reaction variables like type of catalyst and base or reaction time. Furthermore, performance-based parameters (yield, selectivity, turnover number, TON, and turnover frequency, TOF) are considered and evaluated. Findings from ball-milling experimen
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25

Mathias, Fanny, Youssef Kabri, Maxime Crozet, and Patrice Vanelle. "Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydro­imidazo[2,1-b]oxazoles." Synthesis 49, no. 12 (2017): 2775–85. http://dx.doi.org/10.1055/s-0036-1588984.

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A one-pot sequential intramolecular cyclization and Suzuki–Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1-b]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1H-imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki–Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-cataly
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26

Darbem, Mariana P., C. Henrique A. Esteves, Isadora M. de Oliveira, Joel S. Reis, Daniel C. Pimenta, and Hélio A. Stefani. "Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction." RSC Advances 9, no. 17 (2019): 9468–74. http://dx.doi.org/10.1039/c9ra00523d.

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27

Sheshashena Reddy, T., Ramesh Maragani, and Rajneesh Misra. "Triarylborane substituted naphthalimide as a fluoride and cyanide ion sensor." Dalton Transactions 45, no. 6 (2016): 2549–53. http://dx.doi.org/10.1039/c5dt04039f.

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28

Nasseri, Mohammad Ali, Zinat Rezazadeh, Milad Kazemnejadi, and Ali Allahresani. "A Co–Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C–N cross-coupling reactions in water." Dalton Transactions 49, no. 30 (2020): 10645–60. http://dx.doi.org/10.1039/d0dt01846e.

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A novel bimetallic catalytic system based on Cu/Co has been developed and used as an efficient, eco-friendly, and recyclable catalyst for base- and Pd-free Sonogashira, Suzuki and C–N cross-coupling reactions in mild reaction conditions.
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29

Yan, Jia Ying, Ya Qing Feng, Fang Qun Zhou, Yi Wen Chang, and Bao Zhang. "Studies on Sonogashira Coupling Reaction of Dibenzoporphyrin." Advanced Materials Research 581-582 (October 2012): 317–21. http://dx.doi.org/10.4028/www.scientific.net/amr.581-582.317.

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Changing the proportion of NBS and porphyrin, dibromination of β, β’- π-extended porphyrins was found to selectively occur to the β and β’ position of the porphyrins which is antipotal to the fused aromatic ring. Subsequent Sonogashira coupling of the resultant dibromoporphyrin introduced a carboxylphenylethynyl group to the π-extended porphyrin and the π conjugation was thus further elongated. The coupling products have shown a broadening and a red-shift of the Soret band and Q bands in the UV-Vis absorption spectra compared with the π-extended porphyrin starting materials and the original un
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30

Borude, Vasant S., Rikhil V. Shah, and Sanjeev R. Shukla. "Phosphine-free copper-mediated Sonogashira coupling reaction." Monatshefte für Chemie - Chemical Monthly 144, no. 11 (2013): 1663–69. http://dx.doi.org/10.1007/s00706-013-1058-8.

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31

Nakamura, Keiichi, Hitoshi Okubo, and Masahiko Yamaguchi. "ChemInform Abstract: Low Temperature Sonogashira Coupling Reaction." ChemInform 30, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199938109.

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32

Dang, Tuan Thanh, Peter Langer, Nguyen Thi Son, et al. "Synthesis of 5- and 6-Azaindoles by Sequential Site-Selective Palladium-Catalyzed C–C and C–N Coupling Reactions." Synlett 31, no. 13 (2020): 1308–12. http://dx.doi.org/10.1055/s-0040-1707853.

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Two-step sequential procedures for the Pd-catalyzed synthesis of 5- and 6-azaindoles are reported. The reactions proceed in very good yields. 6-Azaindoles are formed through site-selective Pd-catalyzed Sonogashira reaction of 3,4-dibromopyridine with alkynes, followed by a Pd-catalyzed tandem C–N coupling and cyclization with amines. On the other hand, 5-azaindoles are obtained by a site-selective Pd-catalyzed C–N coupling reaction of 3,4-dibromopyridine with amines, followed by C–C coupling and cyclization with alkynes.
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33

Rout, Yogajivan, and Rajneesh Misra. "Design and synthesis of 1,8-naphthalimide functionalized benzothiadiazoles." New Journal of Chemistry 45, no. 22 (2021): 9838–45. http://dx.doi.org/10.1039/d1nj00919b.

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34

Iranpoor, Nasser, Habib Firouzabadi, Somayeh Motevalli, and Khashayar Rajabi. "A Green Approach for Copper-Free Sonogashira Reaction of Aryl Halides with Phenylacetylene in the Presence of Nano-Pd/Phosphorylated Silica (SDPP/Pd0)." Australian Journal of Chemistry 68, no. 6 (2015): 926. http://dx.doi.org/10.1071/ch14332.

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Silicadiphenyl phosphinite (SDPP) is used as the solid support for the generation of nano SDPP/Pd(0) from PdII as pre-catalyst. This nano catalyst was used for the efficient copper-free Sonogashira reaction of aryl halides in PEG-200 as a solvent. The nano Pd(0) that can be used as pre-prepared or as in situ-generated catalyst exhibited excellent reactivity and stability in the Sonogashira cross-coupling reactions with different aryl iodides, bromides, and also chlorides. This heterogeneous catalyst can be easily recovered and reused in several runs. The use of PEG as solvent and K2CO3 as inor
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35

Choi, Jaewon, Ju Hong Ko, Chang Wan Kang, et al. "Enhanced redox activity of a hollow conjugated microporous polymer through the generation of carbonyl groups by carbonylative Sonogashira coupling." Journal of Materials Chemistry A 6, no. 15 (2018): 6233–37. http://dx.doi.org/10.1039/c8ta01379a.

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36

Andrade, Marta A., and Luísa M. D. R. S. Martins. "New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions." Molecules 25, no. 23 (2020): 5506. http://dx.doi.org/10.3390/molecules25235506.

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The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura, Sonogashira, Heck, and others, are powerful tools for carbon–carbon bond formations and have become truly fundamental routes in catalysis, among other fields. Various greener strategies have emerged in recent years, given the widespread popularity of these important reactions. The present review comprises literature from 2015 onward covering the implem
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37

Sharma, Rekha, Prabhat Gautam, Rajneesh Misra та Sanjeev K. Shukla. "β-Substituted triarylborane appended porphyrins: photophysical properties and anion sensing". RSC Advances 5, № 34 (2015): 27069–74. http://dx.doi.org/10.1039/c5ra03931b.

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38

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 (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)benz
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39

Watanabe, Masataka, Shuntaro Mataka, and Thies Thiemann. "One pot Sonogashira-coupling/Wittig olefination procedures." Journal of Chemical Research 2005, no. 10 (2005): 636–39. http://dx.doi.org/10.3184/030823405774663057.

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Bromoarylcarbaldehydes, bromoheteroarylcarbaldehydes, and bromoalkenals can be subjected to a one pot Sonogashira coupling–Wittig olefination reaction to give easy access to molecules with extended pi-systems.
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40

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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41

Arora, Inderpreet, Sandeep K. Sharma, and Arun K. Shaw. "Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars." RSC Advances 6, no. 16 (2016): 13014–26. http://dx.doi.org/10.1039/c5ra26005a.

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Various fuco-configured bicyclic pyrrolidotriazole aglycone mimics were synthesised using copper-catalysed coupling of allyl bromides with terminal alkynes and Sonogashira–Hagihara reaction followed by intramolecular azide-alkyne ‘click’ reaction.
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42

Thanayupong, Eknarin, Khomson Suttisintong, Mongkol Sukwattanasinitt, and Nakorn Niamnont. "Turn-on fluorescent sensor for the detection of cyanide based on a novel dicyanovinyl phenylacetylene." New Journal of Chemistry 41, no. 10 (2017): 4058–64. http://dx.doi.org/10.1039/c6nj03794a.

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43

Fukuyama, Takahide, Ryo Yamaura, and Ilhyong Ryu. "Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6." Canadian Journal of Chemistry 83, no. 6-7 (2005): 711–15. http://dx.doi.org/10.1139/v05-031.

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A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.Key words: carbonylation, palladium, three-component coupling, ionic liquid, α,β-acetylenic ketones.
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44

Rizkin, Benjamin A., and Ryan L. Hartman. "Catalytic activity of Pd/hydrophilic phosphine ligand in the interface of an aqueous-phase Cu-free Sonogashira coupling." Reaction Chemistry & Engineering 3, no. 3 (2018): 251–57. http://dx.doi.org/10.1039/c8re00021b.

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45

Feng, Nianyun, Shujuan Wu, Danna Song, et al. "Conjugated microporous polymer foams with excellent thermal insulation performance in a humid environment." RSC Advances 11, no. 23 (2021): 13957–63. http://dx.doi.org/10.1039/d1ra01616d.

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46

Hussain, Najrul, Pranjal Gogoi, Puja Khare, and Manash R. Das. "Nickel nanoparticles supported on reduced graphene oxide sheets: a phosphine free, magnetically recoverable and cost effective catalyst for Sonogashira cross-coupling reactions." RSC Advances 5, no. 125 (2015): 103105–15. http://dx.doi.org/10.1039/c5ra22601e.

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47

Ferdousi Moon, Jannatul, Mohammad Mizanur Rahman Khan, M. Ashraful Alam, and Muhammad Younus. "Simple synthesis of poly (1,4-bis(dodecyloxy)-2,5-diethynylbenzene)/Pd composites with catalytic activity in Sonogashira coupling reaction." International Journal of Chemical Reactor Engineering 19, no. 4 (2021): 439–46. http://dx.doi.org/10.1515/ijcre-2020-0220.

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Abstract Palladium on the polymeric materials (Pd@polymer) as a catalyst is now very promising due to its great prospect for catalytic application. Such material in the form of composites is found to be stable and can be applied as catalyst in organic synthesis like Sonogashira coupling reaction. In the present work, Pd containing conjugated poly-ynes composites (Poly (1,4-bis(dodecyloxy)-2,5-diethynylbenzene) (Poly-DEB)/Pd) were synthesized by varying the addition of Pd in the range of equivalent weight of 8:4, 8:2 and 8:1, maintaining the fixed amount of 1,4-bis(dodecyloxy)-2,5-diethynylbenz
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48

Xu, Xun-Hui, Wen-Bin Liu, Xue Song, et al. "Chain-end functionalization of living helical polyisocyanides through a Pd(ii)-mediated Sonogashira coupling reaction." Polymer Chemistry 12, no. 33 (2021): 4838–45. http://dx.doi.org/10.1039/d1py00809a.

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49

M, Heravi; Majid, M. Dehghani, V. Zadsirjan, and M. Ghanbarian. "Alkynes as privileged synthons in selected organic name reactions." Current Organic Synthesis 16, no. 2 (2019): 205–43. https://doi.org/10.2174/1570179416666190126100744.

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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 Clic
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Oka, Hideo, Katsuya Kitai, Takeyuki Suzuki, and Yasushi Obora. "N,N-Dimethylformamide-stabilized copper nanoparticles as a catalyst precursor for Sonogashira–Hagihara cross coupling." RSC Advances 7, no. 37 (2017): 22869–74. http://dx.doi.org/10.1039/c6ra27910d.

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