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Journal articles on the topic 'Suzuki Coupling Reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Kotha, Sambasivarao, Milind Meshram, and Nageswara Panguluri. "Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions." Synthesis 51, no. 09 (2019): 1913–22. http://dx.doi.org/10.1055/s-0037-1612418.

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We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.1 Introduction2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol3 Peptide Modificati

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2

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith та Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols". Synthesis 52, № 05 (2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel

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3

Len, Christophe. "Catalysts for Suzuki–Miyaura Coupling Reaction." Catalysts 10, no. 1 (2020): 50. http://dx.doi.org/10.3390/catal10010050.

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4

Bhatt, Nikita, Smriti, Richa Khare, and Monika Kamboj. "Suzuki-Miyaura Cross Coupling Reaction in Various Green Media." Asian Journal of Chemistry 33, no. 9 (2021): 1976–84. http://dx.doi.org/10.14233/ajchem.2021.22584.

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Suzuki-Miyaura cross-coupling reaction is an efficient and utilized method for the direct formation of carbon-carbon bonds. The effectiveness and efficiency of Suzuki-Miyaura cross-coupling reaction and its applications have been the topic of interest for synthetic chemists for the last few decades. Green chemistry is the area where we use eco-friendly products. Suzuki coupling includes palladium or nickel catalyzed coupling reaction, which involves ester of boric acids or simply boric acids with the organic halides or pseudohalide. In recent years, these catalytic systems have been developed

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5

Franzén, Robert, and Youjun Xu. "Review on green chemistry Suzuki cross coupling in aqueous media." Canadian Journal of Chemistry 83, no. 3 (2005): 266–72. http://dx.doi.org/10.1139/v05-048.

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The Suzuki cross-coupling reaction is a very efficient, reliable, and environmentally friendly method for the introduction of novel carboncarbon bonds into molecules. This review summarizes recent advances in the use of the reaction in aqueous media with a focus on different types of ligands and the ligandless protocols currently in use. Several synthetic targets for the reaction have been mentioned. The work summarizes recent results from studies on asymmetric Suzuki reactions performed in organic aqueous mixed solvents.Key words: Suzuki reaction, green chemistry, metal-catalyzed cross-cou

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6

Rocard, Lou, and Piétrick Hudhomme. "Recent Developments in the Suzuki–Miyaura Reaction Using Nitroarenes as Electrophilic Coupling Reagents." Catalysts 9, no. 3 (2019): 213. http://dx.doi.org/10.3390/catal9030213.

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Palladium-catalyzed cross-coupling reactions are nowadays essential in organic synthesis for the construction of C–C, C–N, C–O, and other C-heteroatom bonds. The 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki was awarded for the discovery of these reactions. These great advances for organic chemists stimulated intense research efforts worldwide dedicated to studying these reactions. Among them, the Suzuki–Miyaura coupling (SMC) reaction, which usually involves an organoboron reagent and an organic halide or triflate in the presence of a base and a palladium

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7

Snieckus, Victor, and Claude Quesnelle. "The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls." Synthesis 50, no. 22 (2018): 4413–28. http://dx.doi.org/10.1055/s-0037-1610273.

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A comparative evaluation of the combined directed ortho metalation (DoM)–Suzuki–Miyaura and DoM–Negishi cross-coupling reactions with aryl triflates for the synthesis of substituted biaryls is described. Both ortho-zinc and ortho-boron aryl directed metalation group (DMG = CON(i-Pr)2, OCONEt2, OMOM, NHBoc) substrates were evaluated. The superiority of the DoM–Negishi over the DoM–Suzuki–Miyaura reaction in operational convenience and mild reaction conditions is noted. Orthogonal Negishi and Suzuki–Miyaura with Corriu–Kumada reactions for the synthesis of a teraryl derivative is also reported.

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8

Vaaland, Ingrid Caroline, and Magne Olav Sydnes. "Consecutive Palladium Catalyzed Reactions in One-Pot Reactions." Mini-Reviews in Organic Chemistry 17, no. 5 (2020): 559–69. http://dx.doi.org/10.2174/1570193x16666190716150048.

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Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been us

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9

Friesen, Richard W., and Laird A. Trimble. "Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water." Canadian Journal of Chemistry 82, no. 2 (2004): 206–14. http://dx.doi.org/10.1139/v03-187.

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4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and th

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10

Gujral, Sarbjeet Singh, Smriti Khatri, Poornima Riyal, and Vinod Gahlot. "ChemInform Abstract: Suzuki Cross-Coupling Reaction." ChemInform 44, no. 32 (2013): no. http://dx.doi.org/10.1002/chin.201332262.

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11

Boruah, Preeti Rekha, Abdul Aziz Ali, Bishwajit Saikia, and Diganta Sarma. "A novel green protocol for ligand free Suzuki–Miyaura cross-coupling reactions in WEB at room temperature." Green Chemistry 17, no. 3 (2015): 1442–45. http://dx.doi.org/10.1039/c4gc02522a.

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A highly efficient green protocol for palladium acetate-catalysed ligand-free Suzuki–Miyaura cross-coupling reactions in neat ‘water extract of banana (WEB)’ was developed. Suzuki–Miyaura reaction proceeds in WEB at very short reaction times under ‘ligand/external base/external promoters/organic medium’ free conditions.

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12

Said, Khemais, Ali Mesni, and Ridha B. Salem. "Antioxidant Properties of Synthesis Nanometallic Pd-Ni@2- Mercaptoethanol as Effective Catalyst for Suzuki-Miyaura Reactions." Letters in Organic Chemistry 17, no. 1 (2019): 36–45. http://dx.doi.org/10.2174/1570178616666190319160151.

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The palladium-catalyzed Suzuki coupling reaction is one of the most effcient strategies for constructing a carbon-carbon bond. In recent years, bimetallic catalysts have become candidates for the Suzuki coupling reaction. In this work, Pd-Ni@2-Mercaptoethanol nanoparticles were synthesized for the Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides, in the N,Ndimethylformamide/ water mixture catalyzed by Pd-Ni: A simple and efficient reaction performed in a solvent, without a ligand, and in open air. We found that the Suzuki-Miyaura reactions are remarkably fast (5 min), with

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13

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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14

M. Heravi, Majid, Masoumeh Malmir, and Razieh Moradi. "Recent Advances in the Applications of the Intramolecular Suzuki Cross-coupling Reaction in Cyclization and Heterocyclization: An Update." Current Organic Chemistry 23, no. 22 (2020): 2469–88. http://dx.doi.org/10.2174/1385272823666191023115842.

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: The palladium-catalyzed reaction of aryl halide and boronic acid for the formation of C–C bonds so-called Suzuki–Miyaura cross-coupling reaction has many applications in Modern Synthetic Organic Chemistry. In 2013, we emphasized the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization. Due to a plethora relevant papers appeared in the chemical literature, herein, we wish to cover by updating our previous review, the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization leading to various homocy

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15

Brimble, Margaret A., and Fatiah Issa. "Reaction of Bromonaphthofurans with Bis(pinacolato)diboron." Australian Journal of Chemistry 52, no. 11 (1999): 1021. http://dx.doi.org/10.1071/ch99073.

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The synthesis of a dimeric pyranonaphthoquinone (8) was investigated focusing on a late-stage biaryl coupling of suitably functionalized bromonaphthofurans by using Suzuki–Miyaura methodology. Bromonaphthofuran (16) underwent reaction with bis(pinacolato)diboron in the presence of PdCl2(dppf) to afford boronate ester (21) and furonaphthofuran (22). ‘In situ’coupling of the boronate ester (21) with aryl bromide (16) to the desired dimer (11) was not realized. Bromonaphthofuran (17), prepared by Diels–Alder/retro-Claisen reaction of bromonaphthoquinone (24) with diene (25), underwent Suzuki–Miya

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16

Khabiyev, A. T., and B. S. Selenova. "Palladium(II)-catalyzed Suzuki–Miyaura Reactions of Arylboronic Acid with Aryl Halide in the Presence of Aryl-Ferrocenyl-Phosphines." Eurasian Chemico-Technological Journal 16, no. 1 (2013): 79. http://dx.doi.org/10.18321/ectj172.

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<p>This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these

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17

Basavaraju, Girish, and Ravishankar Rajanna. "Flow Process Development and Optimization of A Suzuki-Miyaura Cross Coupling Reaction using Response Surface Methodology." Bulletin of Chemical Reaction Engineering & Catalysis 15, no. 3 (2020): 604–16. http://dx.doi.org/10.9767/bcrec.15.3.8229.604-616.

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A custom-made tubular flow reactor was utilized to develop a mathematical model and optimize the Suzuki-Miyaura cross coupling reaction. In this study, the experimentation was designed and executed through the statistical design of experiments (DoE) approach via response surface methodology. The effect of molar ratios of phenylboronic acid (1) and 4-bromophenol (2), temperature, the catalyst tetrakis(triphenylphosphine)palladium, and equivalence of aqueous tripotassium phosphate was studied in detail. The flow reactor profile was in good agreement with batch conditions and significant improvem

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18

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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19

Fan, Guozhi, Hanjun Zhang, Siqing Cheng, Zhandong Ren, Zhijun Hu, and Zilan Wang. "Lewis Acid-Promoted Suzuki Reaction using Palladium Chloride Anchored on a Polymer as a Catalyst." Australian Journal of Chemistry 61, no. 8 (2008): 610. http://dx.doi.org/10.1071/ch08066.

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Palladium chloride anchored on polystyrene modified by 5-amino-1,10-phenanthroline was prepared and used as an efficient recoverable catalyst for Suzuki cross-coupling reactions. The heterogeneous catalysts can be easily separated from the reaction mixture and reused for five cycles without significant Pd leaching and loss of catalytic activity. Rate enhancement in the Suzuki reaction by Lewis acids was also studied.

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20

Korenaga, Toshinobu, Takahiro Kosaki, Rokki Fukumura, Tadashi Ema, and Takashi Sakai. "Suzuki−Miyaura Coupling Reaction Using Pentafluorophenylboronic Acid." Organic Letters 7, no. 22 (2005): 4915–17. http://dx.doi.org/10.1021/ol051866i.

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21

Kim, Aram, Ji Chan Park, Mijong Kim, Eunjung Heo, Hyunjoon Song, and Kang Hyun Park. "Suzuki Coupling Reaction Using Hybrid Pd Nanoparticles." Journal of Nanoscience and Nanotechnology 14, no. 2 (2014): 1872–83. http://dx.doi.org/10.1166/jnn.2014.9100.

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22

Qiu, Wenfeng, Shiyan Chen, Xiaobo Sun, Yunqi Liu, and Daoben Zhu. "Suzuki Coupling Reaction of 1,6,7,12-Tetrabromoperylene Bisimide." Organic Letters 8, no. 5 (2006): 867–70. http://dx.doi.org/10.1021/ol052923a.

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23

Cammidge, Andrew N., and Karen V. L. Crépy. "The first asymmetric Suzuki cross-coupling reaction." Chemical Communications, no. 18 (2000): 1723–24. http://dx.doi.org/10.1039/b004513f.

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24

Xu, Chen, Hong-Mei Li, Xiao-Er Yuan, et al. "N-heterocyclic carbene (NHC)-modulated Pd/Cu cocatalyzed three-component synthesis of 2,6-diarylquinolines." Org. Biomol. Chem. 12, no. 19 (2014): 3114–22. http://dx.doi.org/10.1039/c4ob00231h.

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25

Snieckus, Victor, and Claude Quesnelle. "Directed ortho Metalation (DoM)-Linked Corriu–Kumada, Negishi, and Suzuki–Miyaura Cross-Coupling Protocols: A Comparative Study." Synthesis 50, no. 22 (2018): 4395–412. http://dx.doi.org/10.1055/s-0037-1611053.

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A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (DoM) is reported. In general, the Suzuki–Miyaura and Negishi protocols show greater scope and better yields than the Corriu–Kumada variant, although the latter qualitatively proceeds at fastest rate but has low functional group tolerance. The Negishi process is shown to be useful for substrates with nucleophile and base-sensitive functionality and it is comparable to the Suzuki–Miyaura reaction in efficiency. The link of t

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26

Hajipour, Abdol R., and Parisa Abolfathi. "Novel triazole-modified chitosan@nickel nanoparticles: efficient and recoverable catalysts for Suzuki reaction." New Journal of Chemistry 41, no. 6 (2017): 2386–91. http://dx.doi.org/10.1039/c6nj03789e.

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27

Alshammari, Hamed M., Obaid F. Aldosari, Mohammad Hayal Alotaibi, et al. "Facile Synthesis and Characterization of Palladium@Carbon Catalyst for the Suzuki-Miyaura and Mizoroki-Heck Coupling Reactions." Applied Sciences 11, no. 11 (2021): 4822. http://dx.doi.org/10.3390/app11114822.

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Palladium-based carbon catalysts (Pd/C) can be potentially applied as an efficient catalyst for Suzuki–Miyaura and Mizoroki–Heck coupling reactions. Herein, a variety of catalysts of palladium on activated carbon were prepared by varying the content of ‘Pd’ via an in situ reduction method, using hydrogen as a reducing agent. The as-prepared catalysts (0.5 wt % Pd/C, 1 wt % Pd/C, 2 wt % Pd/C and 3 wt % Pd/C) were characterized using X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and Brunauer–Emmett–Teller (BET) analyses. The catalysts wer

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28

Wang, Tao, Shuwu Yang, Silin Xu, Chunyu Han, Ge Guo, and Junfeng Zhao. "Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C–N bond cleavage." RSC Advances 7, no. 26 (2017): 15805–8. http://dx.doi.org/10.1039/c7ra02549a.

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A Pd catalyzed Suzuki cross-coupling of a benzyltrimethylammonium salt is described. This reaction offers a highly efficient approach to diarylmethanes and also paves the way for the application of benzyltrimethylammonium salts in Pd catalyzed cross-coupling reactions.

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29

Kotha, Sambasivarao, Milind Meshram, and Chandravathi Chakkapalli. "Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps." Beilstein Journal of Organic Chemistry 14 (September 21, 2018): 2468–81. http://dx.doi.org/10.3762/bjoc.14.223.

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This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of comple

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30

Hajipour, Abdol R., Parisa Abolfathi, and Fatemeh Mohammadsaleh. "A click strategy for the immobilization of palladium nanoparticles onto silica: efficient and recyclable catalysts for carbon–carbon bond formation under mild reaction conditions." RSC Advances 6, no. 81 (2016): 78080–89. http://dx.doi.org/10.1039/c6ra11734a.

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31

Zhang, Guo Heng, Pei Yu Wang, and Xiu Fang Wei. "Palladium Supported on Functionalized Mesoporous Silica: Synthesis, Structure and Catalytic Properties in Suzuki-Miyaura Coupling Reactions." Advanced Materials Research 750-752 (August 2013): 1083–86. http://dx.doi.org/10.4028/www.scientific.net/amr.750-752.1083.

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Pd nanoparticles supported in functionalized mesoporous silica were prepared. Mesoporous silica support was modified with [3-(2-aminoethyl aminopropyl)] trimethoxysilane. The functionalized mesoporous silica can be loaded with palladium and the resulting material used as a catalyst for the Suzuki-Miyaura coupling reactions. Highly dispersed and uniform palladium nanoparticles could be detected using transmission electron microscopy. The Pd-SBA-15 nanocomposite exhibits an excellent catalytic activity and low Pd leaching for the Suzuki-Miyaura coupling reaction.

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32

Putta, Chandrababu, Vittal Sharavath, Suprabhat Sarkar та Sutapa Ghosh. "Palladium nanoparticles on β-cyclodextrin functionalised graphene nanosheets: a supramolecular based heterogeneous catalyst for C–C coupling reactions under green reaction conditions". RSC Advances 5, № 9 (2015): 6652–60. http://dx.doi.org/10.1039/c4ra14323j.

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Palladium nanoparticles on β-cyclodextrin functionalised graphene based supramolecular heterogeneous catalyst are used for Suzuki–Miyaura and Heck–Mizoroki coupling reactions under green reaction conditions.

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33

Jadhav, Sanjay N., Arjun S. Kumbhar, Chadrashekhar V. Rode, and Rajashri S. Salunkhe. "Ligand-free Pd catalyzed cross-coupling reactions in an aqueous hydrotropic medium." Green Chemistry 18, no. 7 (2016): 1898–911. http://dx.doi.org/10.1039/c5gc02314a.

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A simple, efficient and ligand-free protocol for the Suzuki–Miyaura reaction and base-free Heck–Matsuda reactions under mild reaction conditions has been developed over palladium supported on activated carbon (Pd/C) in an aqueous hydrotropic solution.

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34

Štambaský, Jan, Andrei V. Malkov, and Pavel Kočovský. "Preparation of Boc-Protected Cinnamyl-Type Alcohols: A Comparison of the Suzuki-Miyaura Coupling, Cross-Metathesis, and Horner-Wadsworth-Emmons Approaches and Their Merit in Parallel Synthesis." Collection of Czechoslovak Chemical Communications 73, no. 5 (2008): 705–32. http://dx.doi.org/10.1135/cccc20080705.

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Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadswo

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35

Sharif, Muhammad, Khurram Shoaib, Shahzad Ahmed, et al. "Synthesis of functionalised fluorinated pyridine derivatives by site-selective Suzuki-Miyaura cross-coupling reactions of halogenated pyridines." Zeitschrift für Naturforschung B 72, no. 4 (2017): 263–79. http://dx.doi.org/10.1515/znb-2016-0213.

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AbstractThe Suzuki-Miyaura reaction of 2,6-dichloro-3-(trifluoromethyl)pyridine with 1 equiv of arylboronic acids resulted in site-selective formation of 2-aryl-6-chloro-3-(trifluoromethyl)pyridine. Due to electronic reasons, the reaction takes place at the sterically more hindered position. The selectivity was rationalised by DFT calculations. The one-pot reaction with two different arylboronic acids afforded 2,6-diaryl-3-(trifluoromethyl)pyridine containing two different aryl substituents. The reactions proceeded smoothly in the absence of phosphine ligands. In addition, Suzuki-Miyaura react

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36

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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37

Franzén, Robert. "The Suzuki, the Heck, and the Stille reaction - three versatile methods for the introduction of new C-C bonds on solid support." Canadian Journal of Chemistry 78, no. 7 (2000): 957–62. http://dx.doi.org/10.1139/v00-089.

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Metal-catalyzed coupling reactions are very efficient and reliable methods for the introduction of new carbon-carbon bonds onto molecules attached to a solid support. This review summarizes recent advances in utilizing the three most used methods, the Suzuki reaction, the Heck reaction, and the Stille reaction, in the field of solid phase organic synthesis resulting in small organic molecule libraries.Key words: metal-catalyzed coupling reactions, carbon-carbon bonds, solid phase synthesis, combinatorial chemistry, drug discovery.

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38

Wu, Li, Bin Yuan, Mengmeng Liu, et al. "A facile synthesis of a solvent-dispersible magnetically recoverable Pd0 catalyst for the C–C coupling reaction." RSC Advances 6, no. 61 (2016): 56028–34. http://dx.doi.org/10.1039/c6ra11674d.

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A Pd<sup>0</sup>/Fe<sub>3</sub>O<sub>4</sub>-DA/DMG catalyst exhibited excellent catalytic activity toward the Suzuki, Heck and Kumada cross coupling reaction with a high yield. It is an especially efficient catalyst for Suzuki and Heck coupling in water.

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39

Sarkar, Shaheen M., Md Lutfor Rahman, and Mashitah Mohd Yusoff. "Heck, Suzuki and Sonogashira cross-coupling reactions using ppm level of SBA-16 supported Pd-complex." New Journal of Chemistry 39, no. 5 (2015): 3564–70. http://dx.doi.org/10.1039/c4nj02319f.

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40

Yamada, Tsuyoshi, Jing Jiang, Naoya Ito, et al. "Development of Facile and Simple Processes for the Heterogeneous Pd-Catalyzed Ligand-Free Continuous-Flow Suzuki–Miyaura Coupling." Catalysts 10, no. 10 (2020): 1209. http://dx.doi.org/10.3390/catal10101209.

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The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction of (hetero)aryl iodides, bromides, and chlorides with (hetero)aryl boronic acids was developed using cartridges packed with spherical resin (tertiary amine-based chelate resin: WA30)-supported palladium catalysts (7% Pd/WA30). The void space in the

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Elazab, Hany A., Ali R. Siamaki, B. Frank Gupton, and M. Samy El-Shall. "Pd-Fe3O4/RGO: a Highly Active and Magnetically Recyclable Catalyst for Suzuki Cross Coupling Reaction using a Microfluidic Flow Reactor." Bulletin of Chemical Reaction Engineering & Catalysis 14, no. 3 (2019): 478. http://dx.doi.org/10.9767/bcrec.14.3.3518.478-489.

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There are several crucial issues that need to be addressed in the field of applied catalysis. These issues are not only related to harmful environmental impact but also include process safety concerns, mass and heat transfer limitations, selectivity, high pressure, optimizing reaction conditions, scale-up issues, reproducibility, process reliability, and catalyst deactivation and recovery. Many of these issues could be solved by adopting the concept of micro-reaction technology and flow chemistry in the applied catalysis field. A microwave assisted reduction technique has been used to prepare

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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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Yamamoto, Kyoko, Masataka Watanabe, Kyoko Ideta, Shuntaro Mataka, and Thies Thiemann. "Combined Suzuki Coupling – Wittig Olefination Reaction in Aqueous Medium." Zeitschrift für Naturforschung B 60, no. 12 (2005): 1299–307. http://dx.doi.org/10.1515/znb-2005-1215.

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Watson, Allan, Kirsty Wilson, Jane Murray, and Craig Jamieson. "Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-Coupling." Synlett 29, no. 05 (2017): 650–54. http://dx.doi.org/10.1055/s-0036-1589143.

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The Suzuki–Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C–C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene™ in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.

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Lee, Shao-Chi, Lin Guo, and Magnus Rueping. "Nickel-catalyzed exo-selective hydroacylation/Suzuki cross-coupling reaction." Chemical Communications 55, no. 99 (2019): 14984–87. http://dx.doi.org/10.1039/c9cc07558e.

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Kwon, Young-Bum, Jin-Hyung Park, Bo-Ram Choi, Hyun-Soo Kim, and Cheol-Min Yoon. "Synthesis of 3-Benzylcoumarins Using Suzuki Coupling Reaction." Bulletin of the Korean Chemical Society 32, spc8 (2011): 2897–98. http://dx.doi.org/10.5012/bkcs.2011.32.8.2897.

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Suzuki, Akira. "Organoboranes in Organic Syntheses Including Suzuki Coupling Reaction." HETEROCYCLES 80, no. 1 (2010): 15. http://dx.doi.org/10.3987/com-09-s(s)summary.

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Bai, L., and J. Wang. "Environmentally Friendly Suzuki Aryl-Aryl Cross-Coupling Reaction." Current Organic Chemistry 9, no. 6 (2005): 535–53. http://dx.doi.org/10.2174/1385272053544407.

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Yang, Cuixian, Amy K. Manocchi, Byeongdu Lee, and Hyunmin Yi. "Viral-templated palladium nanocatalysts for Suzuki coupling reaction." J. Mater. Chem. 21, no. 1 (2011): 187–94. http://dx.doi.org/10.1039/c0jm03145c.

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Kirschning, A., W. Solodenko, K. Mennecke, C. Vogt, and S. Gruhl. "Polyvinylpyridine-Supported Palladacycle for the Suzuki Coupling Reaction." Synfacts 2006, no. 9 (2006): 0964. http://dx.doi.org/10.1055/s-2006-949258.

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