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Journal articles on the topic 'Sonogashira cross-coupling reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

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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12

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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13

Mohjer, Fatemeh, Prisa Mofatehnia, Yalda Rangraz, and Majid M. Heravi. "Pd-free, Sonogashira cross-coupling reaction. An update." Journal of Organometallic Chemistry 936 (March 2021): 121712. http://dx.doi.org/10.1016/j.jorganchem.2021.121712.

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14

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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15

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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16

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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17

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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18

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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19

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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20

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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21

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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22

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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23

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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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

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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26

Tian, Ze-Yu, Shi-Meng Wang, Su-Jiao Jia, Hai-Xia Song, and Cheng-Pan Zhang. "Sonogashira Reaction Using Arylsulfonium Salts as Cross-Coupling Partners." Organic Letters 19, no. 19 (2017): 5454–57. http://dx.doi.org/10.1021/acs.orglett.7b02764.

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27

Sikk, Lauri, Jaana Tammiku-Taul, and Peeter Burk. "Computational Study of Copper-Free Sonogashira Cross-Coupling Reaction." Organometallics 30, no. 21 (2011): 5656–64. http://dx.doi.org/10.1021/om2004817.

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28

Ezugwu, Chizoba I., Bibimaryam Mousavi, Md Ali Asrafa, Akshay Mehta, Harsh Vardhan, and Francis Verpoort. "An N-heterocyclic carbene based MOF catalyst for Sonogashira cross-coupling reaction." Catalysis Science & Technology 6, no. 7 (2016): 2050–54. http://dx.doi.org/10.1039/c5cy01944c.

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29

Chronopoulos, Demetrios D., Miroslav Medved’, Piotr Błoński, et al. "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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30

Xu, Yongjie, Reiner Sebastian Sprick, Nick J. Brownbill, et al. "Bottom-up wet-chemical synthesis of a two-dimensional porous carbon material with high supercapacitance using a cascade coupling/cyclization route." Journal of Materials Chemistry A 9, no. 6 (2021): 3303–8. http://dx.doi.org/10.1039/d0ta11649a.

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A 2D porous carbon material with excellent electrochemical performance as an electrode in supercapacitors was synthesised using a Sonogashira–Hagihara cross-coupling/Bergman cyclization cascade reaction.

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31

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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32

Pires, Marina, Sara Purificação, A. Santos, and M. Marques. "The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions." Synthesis 49, no. 11 (2017): 2337–50. http://dx.doi.org/10.1055/s-0036-1589498.

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Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Poly

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33

Sultana, Samim, Swapna Devi Mech, Farhaz Liaquat Hussain, Pallab Pahari, Geetika Borah, and Pradip K. Gogoi. "Green synthesis of graphene oxide (GO)-anchored Pd/Cu bimetallic nanoparticles using Ocimum sanctum as bio-reductant: an efficient heterogeneous catalyst for the Sonogashira cross-coupling reaction." RSC Advances 10, no. 39 (2020): 23108–20. http://dx.doi.org/10.1039/d0ra01189d.

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34

Voltrova, Svatava, and Jiri Srogl. "Sonogashira cross-coupling under non-basic conditions. Flow chemistry as a new paradigm in reaction control." Org. Chem. Front. 1, no. 9 (2014): 1067–71. http://dx.doi.org/10.1039/c4qo00198b.

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35

Bysewski, Oliver, Andreas Winter, and Ulrich S. Schubert. "Catalysis of a Bis-Caffeine Palladium(II) NHC-Pincer Complex." Inorganics 11, no. 4 (2023): 164. http://dx.doi.org/10.3390/inorganics11040164.

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A tridentate bis-NHC Pd complex, based on caffeine, was studied for its catalytic activity. This complex displayed a high catalytic activity in the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions of aryl halides. The Sonogashira cross-coupling was also investigated but reveals a fast plateauing of the reaction. Aryl iodides as well as aryl bromides react when equipped with either electron-donating or electron-withdrawing substituents. Aryl chlorides, which contained electron-withdrawing groups, were also reactive under the applied conditions.

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36

Ros, Enric, Amparo Prades, Dominique Forson, et al. "Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazines via a Sonogashira-type cross-coupling reaction." Chemical Communications 56, no. 75 (2020): 11086–89. http://dx.doi.org/10.1039/d0cc03482g.

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37

Shetty, Suchetha, Noorullah Baig, Atikur Hassan, Saleh Al-Mousawi, Neeladri Das, and Bassam Alameddine. "Fluorinated Iron(ii) clathrochelate units in metalorganic based copolymers: improved porosity, iodine uptake, and dye adsorption properties." RSC Advances 11, no. 25 (2021): 14986–95. http://dx.doi.org/10.1039/d1ra02357h.

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We report the synthesis of metalorganic copolymers made from the palladium catalyzed Sonogashira cross-coupling reaction between various iron(ii) clathrochelate building blocks with diethynyl–triptycene and fluorene derivatives.

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38

Ikeda, A., M. Omote, K. Kusumoto, et al. "A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines." Organic & Biomolecular Chemistry 14, no. 6 (2016): 2127–33. http://dx.doi.org/10.1039/c5ob02558c.

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39

Chen, Jingwen, Haifeng Xiang, Li Yang, and Xiangge Zhou. "Synthesis of 2-substituted benzo[b]thiophene via a Pd-catalyzed coupling of 2-iodothiophenol with phenylacetylene." RSC Advances 7, no. 13 (2017): 7753–57. http://dx.doi.org/10.1039/c6ra26611h.

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40

Li, Gao, and Rongchao Jin. "Catalysis by gold nanoparticles: carbon-carbon coupling reactions." Nanotechnology Reviews 2, no. 5 (2013): 529–45. http://dx.doi.org/10.1515/ntrev-2013-0020.

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AbstractGold nanoparticles have been demonstrated to be efficient catalysts for a wide range of reactions in the past decades, such as oxidation and hydrogenation. In recent research, gold nanoparticle catalysts have been utilized in carbon-carbon coupling reactions. These coupling reactions have been established as convenient and general approaches toward biaryl or propargylamines, which are biologically active compounds, natural products, and pharmaceutical organic compounds. This review aims to highlight the current achievements in the field of gold nanoparticle-catalyzed coupling reactions

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41

Yang, Wen, Yongqi Yao, Xin Yang, Yingying Deng, Qifu Lin, and Dingqiao Yang. "Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction." RSC Advances 9, no. 16 (2019): 8894–904. http://dx.doi.org/10.1039/c9ra00577c.

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A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%).

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42

Yang, Ru Chun, Tao Hu, Xiao Jun Wang, and Qiang Xiao. "Synthesis of Carbohydrate-Conjugated Flavone Derivatives." Advanced Materials Research 1094 (March 2015): 53–56. http://dx.doi.org/10.4028/www.scientific.net/amr.1094.53.

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A series of flavone derivatives conjugated with carbohydrate were synthesized from 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one. The key step is its cross coupling with the carbohydrate under Sonogashira reaction.

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43

Misra, Rajneesh, Thaksen Jadhav, Bhausaheb Dhokale, and Shaikh M. Mobin. "Colorimetric and fluorimetric detection of fluoride and cyanide ions using tri and tetra coordinated boron containing chromophores." Dalton Transactions 44, no. 36 (2015): 16052–60. http://dx.doi.org/10.1039/c5dt02356d.

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Two organoboron based fluorophores pyrazabole 3 and BODIPY 4 have been designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling reaction and successfully employed for fluoride and cyanide ion sensing.

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44

Ashikari, Yosuke, Kei Maekawa, Mai Ishibashi, et al. "Stille, Heck, and Sonogashira coupling and hydrogenation catalyzed by porous-silica-gel-supported palladium in batch and flow." Green Processing and Synthesis 10, no. 1 (2021): 722–28. http://dx.doi.org/10.1515/gps-2021-0069.

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Abstract Owing to their recyclability, heterogeneous transition metal catalysts represent a means of conserving depletable resources for the synthesis of pharmaceutical, agricultural, and functional chemicals. We recently developed a novel heterogeneous palladium catalyst and demonstrated its synthetic availability for Suzuki–Miyaura cross-coupling. Herein, we report the further application of the present catalyst to cross-coupling reactions in batch and flow, as well as a hydrogenative reduction reaction in flow. We demonstrate the flow synthesis for useful material, a liquid crystal, and a 1

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45

Salih, Kifah S. M., and Younis Baqi. "Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond." Catalysts 10, no. 1 (2019): 4. http://dx.doi.org/10.3390/catal10010004.

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Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing palladium or its salts as catalysis have, for decades, attracted and inspired researchers affiliated with academia and industry. Tremendous efforts have been paid to develop and achieve more sustainable reaction conditions, such as the reduction in energy consumption by applying the microwave irradiation technique. Chemical reactions under controlled microwave c

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46

Qian, Deyun, and Junliang Zhang. "Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions." Beilstein Journal of Organic Chemistry 7 (June 15, 2011): 808–12. http://dx.doi.org/10.3762/bjoc.7.92.

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A straightforward, efficient, and reliable redox catalyst system for the Au(I)/Au(III)-catalyzed Sonogashira cross-coupling reaction of functionalized terminal alkynes with arylboronic acids under mild conditions has been developed.

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47

Kim, Young-O., Hyung-Seok Jang, Yo-han Kim, et al. "A tyrosine-rich peptide induced flower-like palladium nanostructure and its catalytic activity." RSC Advances 5, no. 95 (2015): 78026–29. http://dx.doi.org/10.1039/c5ra11817d.

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Flower-like palladium nanostructure (Pd nano-flower) induced by tyrosine-rich peptide, Tyr-Tyr-Ala-His-Ala-Tyr-Tyr (YYAHAYY), showed excellent catalytic activities in copper-free Sonogashira cross-coupling reaction in water.

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48

Wu, You, Yongning Xing, Jie Wang, Qi Sun, Weiqi Kong, and Franck Suzenet. "Palladium-catalyzed desulfurative Sonogashira cross-coupling reaction of 3-cyano assisted thioamide-type quinolone derivatives with alkynes." RSC Advances 5, no. 60 (2015): 48558–62. http://dx.doi.org/10.1039/c5ra06337j.

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A Pd-catalyzed Cu-mediated desulfurative Sonogashira cross-coupling reaction of thioamide-type quinolone derivatives was proposed for the construction of C<sub>sp</sub><sup>2</sup>–C<sub>sp</sub> bonds.

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49

Karuo, Yukiko, Keita Hirata, Atsushi Tarui, Kazuyuki Sato, Kentaro Kawai, and Masaaki Omote. "Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers." Beilstein Journal of Organic Chemistry 20 (October 24, 2024): 2691–703. http://dx.doi.org/10.3762/bjoc.20.226.

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In this study, we develop the synthesis methods of fluoroalkenes and fluoroenynes via Suzuki–Miyaura and Sonogashira cross-coupling reactions using novel multihalogenated fluorovinyl ethers, which are easily prepared from the reaction between phenols and 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane). These reactions make use of the unique structure of multihalogenated fluorovinyl ethers, which contains a reactive bromine atom, to afford a series of fluoroalkenes and fluoroenynes in moderate to high yields.

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50

Yang, Bingchuan, Guodong Shen, Xianqiang Huang, and Rutao Liu. "Design and Synthesis of a Novel Banana-Shaped Functional Molecule via Double Cross-Coupling." Molecules 24, no. 4 (2019): 698. http://dx.doi.org/10.3390/molecules24040698.

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A novel banana-shaped molecule using 2,8-Dimethyl-6H,12H-5,11-methanodibenzo [b,f] [1,5]diazocine (Tröger’s base) as bent-core was synthesized via double Carbon-Carbon cross-coupling reaction. The double Sonogashira cross-coupling reaction was optimized by using Pd(PPh3)2Cl2 as catalyst, CuI as cocatalyst and diisopropylamine as base in place of triethylamine. The structure of this compound was confirmed by 1H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry.

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