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Journal articles on the topic 'Sonogashira coupling reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

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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2

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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3

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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4

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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5

Nair, Pravya P., Rose Mary Philip, and Gopinathan Anilkumar. "Nickel catalysts in Sonogashira coupling reactions." Organic & Biomolecular Chemistry 19, no. 19 (2021): 4228–42. http://dx.doi.org/10.1039/d1ob00280e.

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6

Pan, Changduo, Fang Luo, Wenhui Wang, Zhishi Ye, and Miaochang Liu. "Iron-catalysed Sonogashira Reactions." Journal of Chemical Research 2009, no. 8 (2009): 478–81. http://dx.doi.org/10.3184/030823409x465295.

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A catalytic system has been developed that used an iron/ligand combination for the Sonogashira cross coupling of terminal alkynes with aryl iodides, which affords products in good to excellent yields.

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7

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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8

Aronica, Laura, and Gianluigi Albano. "Cyclization Reactions for the Synthesis of Phthalans and Isoindolines." Synthesis 50, no. 06 (2018): 1209–27. http://dx.doi.org/10.1055/s-0037-1609175.

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Oxygen and nitrogen heterocycles are present in a vast number of natural substrates and biologically active molecules. In particular, phthalan and isoindoline subunits are found in many classes of products such as antibiotics, antioxidants, antimycotics, pigments, and fluorophores. Therefore several procedures dedicated to the construction of these heterocycles have been developed. In this review, a detailed analysis of the literature data regarding the synthesis of these nuclei via cyclization reactions is reported.1 Introduction2 Phthalans2.1 Oxa-Pictet–Spengler Reaction2.2 Garratt–Braverman

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9

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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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

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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12

Ohtaka, Atsushi. "Transition-metal Nanoparticles Catalyzed Carbon-Carbon Coupling Reactions in Water." Current Organic Chemistry 23, no. 6 (2019): 689–703. http://dx.doi.org/10.2174/1385272823666190419211714.

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The use of transition-metal nanoparticles in catalysis has attracted much interest, and their use in carbon-carbon coupling reactions such as Suzuki, Heck, Sonogashira, Stille, Hiyama, and Ullmann coupling reactions constitutes one of their most important applications. The transition-metal nanoparticles are considered as one of the green catalysts because they show high catalytic activity for several reactions in water. This review is devoted to the catalytic system developed in the past 10 years in transition-metal nanoparticles-catalyzed carbon-carbon coupling reactions such as Suzuki, Heck,

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13

Petuker, Anette, Mohamed El-Tokhey, Matthew L. Reback, Bert Mallick, and Ulf-Peter Apfel. "Towards Iron-Catalyzed Sonogashira Cross-Coupling Reactions." ChemistrySelect 1, no. 11 (2016): 2717–21. http://dx.doi.org/10.1002/slct.201600771.

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14

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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15

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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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

Reimann, Sebastian, Peter Ehlers, Lars Ohlendorf, and Peter Langer. "Sonogashira cross-coupling reactions of 3,5-dibromo-2,6-dichloropyridine." Organic & Biomolecular Chemistry 15, no. 6 (2017): 1510–20. http://dx.doi.org/10.1039/c6ob02264b.

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18

Larson, Gerald. "Some Aspects of the Chemistry of Alkynylsilanes." Synthesis 50, no. 13 (2018): 2433–62. http://dx.doi.org/10.1055/s-0036-1591979.

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In amongst the considerable chemistry of acetylenes there lies some unique chemistry of alkynylsilanes (silylacetylenes) some of which is reviewed herein. This unique character is exemplified not only in the silyl protection of the terminal C–H of acetylenes, but also in the ability of the silyl group to be converted into other functionalities after reaction of the alkynylsilane and to its ability to dictate and improve the regioselectivity of reactions at the triple bond. This, when combined with the possible subsequent transformations of the silyl group, makes their chemistry highly versatil

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19

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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20

Thomas, Anns Maria, Asha Sujatha, and Gopinathan Anilkumar. "Recent advances and perspectives in copper-catalyzed Sonogashira coupling reactions." RSC Adv. 4, no. 42 (2014): 21688–98. http://dx.doi.org/10.1039/c4ra02529f.

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21

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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22

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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23

Koester, Dennis C., and Daniel B. Werz. "Sonogashira–Hagihara reactions of halogenated glycals." Beilstein Journal of Organic Chemistry 8 (May 2, 2012): 675–82. http://dx.doi.org/10.3762/bjoc.8.75.

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Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2.

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24

Zhang, Ran, Guoqing Lyu, Deng Yuan Li, Pei Nian Liu, and Nian Lin. "Template-controlled Sonogashira cross-coupling reactions on a Au(111) surface." Chemical Communications 53, no. 10 (2017): 1731–34. http://dx.doi.org/10.1039/c6cc10091k.

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25

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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26

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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27

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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28

Sain, Shalu, Sonika Jain, Manish Srivastava, Rajendra Vishwakarma, and Jaya Dwivedi. "Application of Palladium-Catalyzed Cross-Coupling Reactions in Organic Synthesis." Current Organic Synthesis 16, no. 8 (2020): 1105–42. http://dx.doi.org/10.2174/1570179416666191104093533.

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: Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki–Miyaura, Negishi, Sonogashira, Buchwald–Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.

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29

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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30

Setsune, Jun-ichiro. "Palladium chemistry in recent porphyrin research." Journal of Porphyrins and Phthalocyanines 08, no. 01 (2004): 93–102. http://dx.doi.org/10.1142/s1088424604000088.

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Palladium-catalyzed reactions such as Sonogashira coupling, Suzuki coupling, Stille coupling, Heck reactions, and Glaser-Hey oxidation were used to construct porphyrin modules of nano-scale molecular size in recent years. Recent developments in the supramolecular assembly of porphyrins and Pd (II) and in the organopalladium complexes of various porphyrins are also summarized.

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31

Orha, László, József M. Tukacs, László Kollár та László T. Mika. "Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids". Beilstein Journal of Organic Chemistry 15 (3 грудня 2019): 2907–13. http://dx.doi.org/10.3762/bjoc.15.284.

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It was demonstrated that the γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate as a partially bio-based solvent can be utilized as alternative reaction medium for copper- and auxiliary base-free Pd-catalyzed Sonogashira coupling reactions of aryl iodides and functionalized acetylenes under mild conditions. Twenty-two cross-coupling products were isolated with good to excellent yields (72–99%) and purity (>98%). These results represent an example which proves that biomass-derived safer solvents can be utilized efficiently in common, industrially important transformat

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32

Dhage, Ganesh Raosaheb, Santosh Rangnath Deshmukh, and Shankar Ramchandra Thopate. "Synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate and its application in the synthesis of 4-(aryl/heteroaryl/alkynyl)phthalazin-1(2H)-one." RSC Advances 5, no. 42 (2015): 33377–84. http://dx.doi.org/10.1039/c5ra03390j.

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33

Dey, Supriya, and Narayanaswamy Jayaraman. "Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine." Beilstein Journal of Organic Chemistry 8 (April 10, 2012): 522–27. http://dx.doi.org/10.3762/bjoc.8.59.

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This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and So

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34

Torres, I., J. R. Carrillo, A. Díaz-Ortiz, et al. "Self-assembly of T-shape 2H-benzo[d][1,2,3]-triazoles. Optical waveguide and photophysical properties." RSC Advances 6, no. 43 (2016): 36544–53. http://dx.doi.org/10.1039/c6ra02473d.

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35

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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36

Evangelisti, Claudio, Gaetano Angelici, Gianluca Casotti, et al. "Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts." Synthesis 52, no. 12 (2020): 1795–803. http://dx.doi.org/10.1055/s-0039-1690852.

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Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization of the Sonogashira couplings allowed the use of catalysts supported on different matrices with good results in terms of catalytic efficiency and yields.

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37

Jia, Xicheng, Dahong Jiang, Daniel C. W. Tsang, Jungkyu Choi, and Alex C. K. Yip. "Stacking MFI zeolite structures for improved Sonogashira coupling reactions." Microporous and Mesoporous Materials 276 (March 2019): 147–53. http://dx.doi.org/10.1016/j.micromeso.2018.09.039.

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38

an der Heiden, Markus, and Herbert Plenio. "The effect of steric bulk in Sonogashira coupling reactions." Chem. Commun., no. 9 (2007): 972–74. http://dx.doi.org/10.1039/b616608c.

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39

Torborg, Christian, Jun Huang, Thomas Schulz, et al. "Improved Palladium-Catalyzed Sonogashira Coupling Reactions of Aryl Chlorides." Chemistry - A European Journal 15, no. 6 (2009): 1329–36. http://dx.doi.org/10.1002/chem.200802444.

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40

Appukkuttan, Prasad, Wim Dehaen, and Erik Van der Eycken. "Transition-Metal-Free Sonogashira-Type Coupling Reactions in Water." European Journal of Organic Chemistry 2003, no. 24 (2003): 4713–16. http://dx.doi.org/10.1002/ejoc.200300587.

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41

Ali, Imran, Dnyaneshwar Nighot, Mohammad Nadeem Lone, and Arvind Jain. "Efficient copper-catalyzed Sonogashira coupling reactions and simulation studies." Synthetic Communications 47, no. 12 (2017): 1175–84. http://dx.doi.org/10.1080/00397911.2017.1319488.

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42

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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43

Erdélyi, Máté, and Adolf Gogoll. "Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase." Journal of Organic Chemistry 68, no. 16 (2003): 6431–34. http://dx.doi.org/10.1021/jo034284s.

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44

Peng, Hui, Ya-Qin Chen, Shu-Lan Mao, et al. "A general catalyst for Suzuki–Miyaura and Sonogashira reactions of aryl and heteroaryl chlorides in water." Org. Biomol. Chem. 12, no. 35 (2014): 6944–52. http://dx.doi.org/10.1039/c4ob00846d.

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45

Arambasic, Milan, Manjeet K. Majhail, Robert N. Straker, James D. Neuhaus, and Michael C. Willis. "A rhodium-catalysed Sonogashira-type coupling exploiting C–S functionalisation: orthogonality with palladium-catalysed variants." Chemical Communications 55, no. 19 (2019): 2757–60. http://dx.doi.org/10.1039/c9cc00092e.

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Wang, Kaixuan, Liping Yang, Weiliang Zhao, Linqing Cao, Zhenliang Sun, and Fang Zhang. "A facile synthesis of copper nanoparticles supported on an ordered mesoporous polymer as an efficient and stable catalyst for solvent-free sonogashira coupling Reactions." Green Chemistry 19, no. 8 (2017): 1949–57. http://dx.doi.org/10.1039/c7gc00219j.

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Elavarasan, S., B. Baskar, C. Senthil, et al. "An efficient mesoporous carbon nitride (g-C3N4) functionalized Pd catalyst for carbon–carbon bond formation reactions." RSC Advances 6, no. 55 (2016): 49376–86. http://dx.doi.org/10.1039/c6ra04170a.

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Sarkar, Shaheen M., Md Lutfor Rahman, and Mashitah Mohd Yusoff. "Highly active thiol-functionalized SBA-15 supported palladium catalyst for Sonogashira and Suzuki–Miyaura cross-coupling reactions." RSC Advances 5, no. 2 (2015): 1295–300. http://dx.doi.org/10.1039/c4ra13322f.

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Abstract:

SBA-15 supported heterogeneous Pd-catalyst was prepared and applied towards Sonogashira and Suzuki–Miyaura cross-coupling reactions of activated and inactivated aryl halides to give the corresponding coupling products in up to 98% yield.

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Wei, Zhen, Zunyuan Xie, Lingxiang Gao, et al. "Highly Crystallized Pd/Cu Nanoparticles on Activated Carbon: An Efficient Heterogeneous Catalyst for Sonogashira Cross-Coupling Reaction." Catalysts 10, no. 2 (2020): 192. http://dx.doi.org/10.3390/catal10020192.

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Abstract:

In the quest for efficient and recyclable heterogeneous catalysts for Sonogashira coupling reactions, a PEG-OMe (Methoxy Polyene Glycol) - mediated method was developed to immobilize Pd/Cu bimetallic nanoparticles on activated carbon (AC). Catalytic experiments showed that Pd/Cu@AC prepared in a PEG-OMe 500 had the highest activity. The morphology and composition of the catalyst were determined, and the identified crystallized and heterometallic nanoparticles of Pd/Cu were essential for an efficient catalytic cycle. The Pd/Cu@AC catalyst was successfully used in Sonogashira reactions (21 examp

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Al-Zoubi, Raed M., Mothana K. Al-Omari, Walid K. Al-Jammal, and Michael J. Ferguson. "Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions." RSC Advances 10, no. 28 (2020): 16366–76. http://dx.doi.org/10.1039/d0ra01569e.

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