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Journal articles on the topic 'Suzuki Coupling'

Author: Grafiati
Published: 4 June 2021
Last updated: 10 March 2023

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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 (March 25, 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 Modification Using a Ring-Closing Metathesis Strategy4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder­ Reaction as Key Steps8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions9 Modified Peptides via Negishi Coupling10 A Modified Dipeptide via Ethyl Isocyanoacetate11 Conclusions
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2

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith, and Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols." Synthesis 52, no. 05 (January 7, 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 Catalysis2.2 Direct Activation of the C–O Bond2.2.1 Nickel Catalysis3 Suzuki–Miyaura-Type Cross-Coupling Reactions of Benzylic Alcohols4 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allylic Alcohols4.1 Rhodium Catalysis4.2 Palladium Catalysis4.3 Nickel Catalysis4.4 Stereospecific Reactions4.5 Stereoselective Reactions4.6 Domino Reactions5 Suzuki–Miyaura-Type Cross-Coupling Reactions of Propargylic Alcohols5.1 Palladium Catalysis5.2 Rhodium Catalysis6 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allenic Alcohols6.1 Palladium Catalysis6.2 Rhodium Catalysis7 Conclusions
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3

Neufeldt, Sharon R., and John E. A. Russell. "C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives." Synlett 32, no. 15 (May 8, 2021): 1484–91. http://dx.doi.org/10.1055/a-1503-6330.

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AbstractChemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross-couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C–O-selective Ni-catalyzed Suzuki–Miyaura coupling of chloroaryl tosylates is discussed in detail.1 Introduction2 Density Functional Theory Studies on Oxidative Addition at Nickel(0)3 Stoichiometric Oxidative Addition Studies4 Development of a Tosylate-Selective Suzuki Coupling5 Conclusion and Outlook
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4

Barde, E., A. Guérinot, and J. Cossy. "α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions." Synthesis 51, no. 01 (December 7, 2018): 178–84. http://dx.doi.org/10.1055/s-0037-1611358.

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Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Cross-Coupling2.1 Palladium Catalysis2.2 Nickel Catalysis3 Kumada–Corriu Cross-Coupling3.1 Nickel Catalysis3.2 Iron Catalysis3.3 Cobalt Catalysis4 Negishi Cross-Coupling5 Hiyama Cross-Coupling6 Conclusion
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5

SUZUKI, Akira. "Organoborane coupling reactions (Suzuki coupling)." Proceedings of the Japan Academy, Series B 80, no. 8 (2004): 359–71. http://dx.doi.org/10.2183/pjab.80.359.

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6

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 in a green environment for Suzuki reaction (Suzuki-Miyaura cross-coupling reaction). This review epitomizes the Suzuki-Miyaura cross-coupling reaction using efficient catalysts in various green media.
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7

Buchspies, Jonathan, and Michal Szostak. "Recent Advances in Acyl Suzuki Cross-Coupling." Catalysts 9, no. 1 (January 8, 2019): 53. http://dx.doi.org/10.3390/catal9010053.

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Acyl Suzuki cross-coupling involves the coupling of an organoboron reagent with an acyl electrophile (acyl halide, anhydride, ester, amide). This review provides a timely overview of the very important advances that have recently taken place in the acylative Suzuki cross-coupling. Particular emphasis is directed toward the type of acyl electrophiles, catalyst systems and new cross-coupling partners. This review will be of value to synthetic chemists involved in this rapidly developing field of Suzuki cross-coupling as well as those interested in using acylative Suzuki cross-coupling for the synthesis of ketones as a catalytic alternative to stoichiometric nucleophilic additions or Friedel-Crafts reactions.
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8

Ferrer Flegeau, Emmanuel, Matthew E. Popkin, and Michael F. Greaney. "Suzuki Coupling of Oxazoles." Organic Letters 8, no. 12 (June 2006): 2495–98. http://dx.doi.org/10.1021/ol060591j.

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9

Steven, Alan. "Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates." Synthesis 51, no. 13 (May 21, 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 catalyst loading, and safety over the use of organic solvents, irrespective of the setting in which they are used.1 Introduction2 Micelles as Solubilising Agents3 Micelles as Nanoreactors4 Designer Surfactants5 A Critical Evaluation of the Case for Chemistry in Micelles6 Scope of Review7 Suzuki–Miyaura Coupling8 Miyaura Borylation9 Sonogashira Coupling10 Transition-Metal-Catalysed CAr–N Couplings11 SNAr12 Amidation13 Nitro Reduction14 Micellar Sequences15 Summary and Outlook
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10

Çakır, Sinem, Serdar Batıkan Kavukcu, Hande Karabıyık, Senthil Rethinam, and Hayati Türkmen. "C(acyl)–C(sp2) and C(sp2)–C(sp2) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes." RSC Advances 11, no. 60 (2021): 37684–99. http://dx.doi.org/10.1039/d1ra07231e.

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Nitrile-functionalized Pd(ii) complexes have evaluated for the Suzuki–Miyaura cross-coupling reactions. The highest TON value was reached for the acylative Suzuki–Miyaura cross-coupling reaction of acyl chlorides with phenylboronic acids.
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11

Thiemann, Thies, Kuniharu Umeno, Daisuke Ohira, Eiko Inohae, Tsuyoshi Sawada, and Shuntaro Mataka. "Suzuki–Kumada coupling of bromoaroylmethylidenephosphoranes." New Journal of Chemistry 23, no. 11 (1999): 1067–70. http://dx.doi.org/10.1039/a907470h.

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12

Ojida, Akio, Hiroshi Tsutsumi, Noriyuki Kasagi, and Itaru Hamachi. "Suzuki coupling for protein modification." Tetrahedron Letters 46, no. 19 (May 2005): 3301–5. http://dx.doi.org/10.1016/j.tetlet.2005.03.094.

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13

Ricciardi, Roberto, Jurriaan Huskens, and Willem Verboom. "Dendrimer-encapsulated Pd nanoparticles as catalysts for C–C cross-couplings in flow microreactors." Organic & Biomolecular Chemistry 13, no. 17 (2015): 4953–59. http://dx.doi.org/10.1039/c5ob00289c.

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Dendrimer-encapsulated Pd nanoparticles anchored within continuous flow microreactors are efficient for C–C cross-coupling reactions. This is witnessed by the good catalytic performance for the Heck–Cassar and Suzuki–Miyaura couplings.
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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 (January 8, 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 homocyclic and heterocyclic compounds reported during a period of 2013 to 2018.
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15

Wu, Li, Bin Yuan, Mengmeng Liu, Hongfei Huo, Yu Long, Jiantai Ma, and Gongxuan Lu. "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 Pd0/Fe3O4-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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16

Mukai, Shoma, and Yusuke Yamada. "Catalyst Recycling in the Suzuki Coupling Reaction: Toward a Greener Synthesis in the Pharmaceutical Industry." Knowledge 3, no. 1 (December 27, 2022): 1–17. http://dx.doi.org/10.3390/knowledge3010001.

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The Suzuki coupling is a transition metal-catalyzed, cross-coupling carbon–carbon (C–C) bond forming reaction between organic boron compounds and organic halides. As an operationally simple and versatilely applicable procedure, the Suzuki coupling reaction has found immense applications in drug discovery and development in the pharmaceutical industry. Recently, the topic of catalyst recycling has undergone intensive investigations with ever-growing interest in eco-friendly and sustainable synthesis. To recapitulate the latest progress in catalyst recycling in the Suzuki coupling reaction, this invited paper reviews key principles, benefits, challenges, and cutting-edge applications of recyclable catalysts for green synthesis of industrially valuable bioactive molecules. This review paper also discusses how artificial intelligence (AI) could further advance green synthesis of pharmaceutical products.
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17

Kojima, Tatsuo, Shuichi Hiraoka, and Kazuho Ogata. "Selective Preparation of C 2v -Symmetric Hexaphenylbenzene Derivatives through Sequential Suzuki Coupling." Synlett 29, no. 12 (May 29, 2018): 1597–600. http://dx.doi.org/10.1055/s-0037-1610024.

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We have developed effective reaction conditions for the ­Suzuki cross-coupling of chlorinated hexaphenylbenzene derivatives. A chloro group on a hexaphenylbenzene framework exhibits a low reactivity to Suzuki cross-coupling, and only nickel catalysts bearing alkyl-substituted phosphine ligands achieved the coupling. With this as a key step, we succeeded in the selective preparation of a C 2v -symmetric hexaphenylbenzene derivative containing two kinds of aryl group.
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18

Hoffmann, Ina, Bettina Blumenröder, Silvia Onodi neé Thumann, Sabine Dommer, and Jürgen Schatz. "Suzuki cross-coupling in aqueous media." Green Chemistry 17, no. 7 (2015): 3844–57. http://dx.doi.org/10.1039/c5gc00794a.

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19

Lee, Jae Wook, Hyung-Ho Ha, Marc Vendrell, Jacqueline T. Bork, and Young-Tae Chang. "Combinatorial Solid-Phase Synthesis of 6-Aryl-1,3,5-triazines via Suzuki Coupling." Australian Journal of Chemistry 64, no. 5 (2011): 540. http://dx.doi.org/10.1071/ch11034.

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A synthetic methodology to prepare collections of trisubstituted aryl 1,3,5-triazines with broad structural diversity via Suzuki coupling has been developed. We first optimized the combinatorial derivatization of the triazine core using Suzuki cross-coupling. Second, in order to further expand the methodology for the preparation of negatively charged triazines, we adapted this approach to polymer-supported amino acids and prepared aryl triazines with different charge distribution. With a collection of 160 aryl triazine derivatives in good purities and without any purification step, we proved the viability of this orthogonal scheme for the preparation of triazine libraries using amine/amino acid-captured solid supports and Suzuki cross-coupling.
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20

Franzén, Robert, and Youjun Xu. "Review on green chemistry — Suzuki cross coupling in aqueous media." Canadian Journal of Chemistry 83, no. 3 (March 1, 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 carbon–carbon 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-coupling reactions, aqueous synthesis media.
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21

Vinci, Daniele, Nelson Martins, Ourida Saidi, John Bacsa, Amadeu Brigas, and Jianliang Xiao. "Ferrocenyl phosphine–oxazaphospholidine oxide ligands for the Suzuki–Miyaura coupling of hindered aryl bromides and chlorides." Canadian Journal of Chemistry 87, no. 1 (January 1, 2009): 171–75. http://dx.doi.org/10.1139/v08-113.

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A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki–Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.Key words: Suzuki–Miyaura coupling, ferrocenyl phosphines, aryl bromides, aryl chlorides, palladium.
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22

Seo, Tamae, Tatsuo Ishiyama, Koji Kubota, and Hajime Ito. "Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry." Chemical Science 10, no. 35 (2019): 8202–10. http://dx.doi.org/10.1039/c9sc02185j.

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23

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

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24

Wang, Yuanhao, Yunfei Wu, Yuanhe Li, and Yefeng Tang. "Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids." Chemical Science 8, no. 5 (2017): 3852–57. http://dx.doi.org/10.1039/c7sc00367f.

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Palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki reactions of benzotriazoles with boronic acids have been achieved through the in situ generation of ortho-amino-arenediazonium species.
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25

Davis, Mia, Mathias O. Senge, and Oliver B. Locos. "Anthracenylporphyrins." Zeitschrift für Naturforschung B 65, no. 12 (December 1, 2010): 1472–84. http://dx.doi.org/10.1515/znb-2010-1211.

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We report the synthesis and characterization of meso-anthracenylporphyrins with zinc and nickel metal centers. A variety of novel aryl and alkyl meso-substituted anthracenylporphyrins were synthesized via step-wise Suzuki cross-coupling reactions using anthracenyl boronates. This method was compared to standard syntheses based on condensation reactions to yield anthracenylporphyrins of the A2B2- and A3B-type. The work was complemented by the synthesis of a number of the functionalized anthracene derivatives via Suzuki couplings. Selected systems were subjected to single-crystal X-ray analysis which revealed an unusual close packing for nickel(II) anthracenylporphyrins.
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26

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 (December 12, 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 high yields and the products are highly pure. The Pd-Ni@2-Mercaptoetanol nanoparticles have a narrow size distribution with a mean crystallite size of 10 nm. Radical scavenging activities of the complexes have been evaluated by using DPPH, DMPD+ and ABTS+ assays. IC50 values (µg/ml) of the complexes and standards on DPPH, DMPD+ and ABTS+ respectively following the sequences.
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27

Singh Gujral, Sarbjeet, Smriti Khatri, Poornima Riyal, and Vinod Gahlot. "Suzuki Cross Coupling Reaction- A Review." Indo Global Journal of Pharmaceutical Sciences 02, no. 04 (2012): 351–67. http://dx.doi.org/10.35652/igjps.2012.41.

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Suzuki cross coupling reaction is one of the most famous reaction in the field of chemistry. It is a very effective method for making carbon – carbon bonds. It has been extensively utilized in the synthesis of many carbon molecules including the most complex ones. It also find application in the synthesis of compounds of biological sources like (+)-dynemicin, Adragmacidin F, Flurbiprofen, Felbinac, Fenbufen, Difunisal, Aporphinoids, Oximidine II, Nemertelline, Gymnocin A, Palytoxin, Michellamine, CP263,114, Halenaquinone, Brevetoxin, Yuehchukene, caparratriene etc which have been synthesized using the same reaction along with some other organic compounds. The present review article emphasis on carbon-carbon bond formation via cross coupling reaction, mechanism and applications in a natural product synthesis. © 2011 IGJPS. All rights reserved
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28

Liu, Qiancai, Jun Zhang, Peijun Ye, Lu He, and Ting Yuan. "Bifurans via Palladium-Catalyzed Suzuki Coupling." HETEROCYCLES 91, no. 11 (2015): 2190. http://dx.doi.org/10.3987/com-15-13318.

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29

Yadav, M. Ramu, Masahiro Nagaoka, Myuto Kashihara, Rong-Lin Zhong, Takanori Miyazaki, Shigeyoshi Sakaki, and Yoshiaki Nakao. "The Suzuki–Miyaura Coupling of Nitroarenes." Journal of the American Chemical Society 139, no. 28 (July 5, 2017): 9423–26. http://dx.doi.org/10.1021/jacs.7b03159.

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30

Molander, G., and D. Petrillo. "Suzuki-Miyaura Cross-Coupling of Trifluoroboratohomoenolates." Synfacts 2008, no. 7 (July 2008): 0741. http://dx.doi.org/10.1055/s-2008-1077837.

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31

Chen, Qianwei, Shufeng Wu, Shuqin Yan, Chengxi Li, Hayrul Abduhulam, Yanhui Shi, Yanfeng Dang, and Changsheng Cao. "Suzuki–Miyaura Cross-Coupling of Sulfoxides." ACS Catalysis 10, no. 15 (June 30, 2020): 8168–76. http://dx.doi.org/10.1021/acscatal.0c01462.

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32

Gravett, Edward C., Philip J. Hilton, Keith Jones, and Fernando Romero. "A Suzuki coupling approach to bufadienolides." Tetrahedron Letters 42, no. 51 (December 2001): 9081–84. http://dx.doi.org/10.1016/s0040-4039(01)01980-3.

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33

Soderquist, John A., and Juan C. Colberg. "Trans-vinylsilanes via Suzuki-Miyaura coupling." Tetrahedron Letters 35, no. 1 (January 1994): 27–28. http://dx.doi.org/10.1016/0040-4039(94)88153-7.

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34

Soderquist, John A., Karl Matos, Anil Rane, and Jorge Ramos. "Alkynylboranes in the Suzuki-Miyaura coupling." Tetrahedron Letters 36, no. 14 (April 1995): 2401–2. http://dx.doi.org/10.1016/0040-4039(95)00322-4.

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35

Fihri, Aziz, Mohamed Bouhrara, Bijan Nekoueishahraki, Jean-Marie Basset, and Vivek Polshettiwar. "Nanocatalysts for Suzuki cross-coupling reactions." Chemical Society Reviews 40, no. 10 (2011): 5181. http://dx.doi.org/10.1039/c1cs15079k.

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36

Le, Thanh-Ngoc, Theresa Trevisan, Elizabeth Lieu, and David J. R. Brook. "Suzuki-Miyaura Coupling of Verdazyl Radicals." European Journal of Organic Chemistry 2017, no. 7 (February 17, 2017): 1125–31. http://dx.doi.org/10.1002/ejoc.201601483.

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37

Kojima, Akihiko, Shinobu Honzawa, Christopher D. J. Boden, and Masakatsu Shibasaki. "Tandem Suzuki cross-coupling-Heck reactions." Tetrahedron Letters 38, no. 19 (May 1997): 3455–58. http://dx.doi.org/10.1016/s0040-4039(97)00644-8.

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38

Gujral, Sarbjeet Singh, Smriti Khatri, Poornima Riyal, and Vinod Gahlot. "ChemInform Abstract: Suzuki Cross-Coupling Reaction." ChemInform 44, no. 32 (July 18, 2013): no. http://dx.doi.org/10.1002/chin.201332262.

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39

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–Miyaura coupling to naphthofuran (27) and boronate ester (28). Numerous attempts to alter the reaction conditions to effect homocoupling of bromide (17) to biaryl (19) were unsuccessful. Bromopyranonaphthoquinone (18) prepared by oxidative rearrangement of (17) failed to undergo Suzuki–Miyaura coupling.
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40

Yamada, Kohei, Naoto Kamimura, and Munetaka Kunishima. "Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid." Beilstein Journal of Organic Chemistry 13 (July 27, 2017): 1478–85. http://dx.doi.org/10.3762/bjoc.13.146.

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A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.
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41

Clavé, Guillaume, Franck Pelissier, Stéphane Campidelli, and Claude Grison. "Ecocatalyzed Suzuki cross coupling of heteroaryl compounds." Green Chemistry 19, no. 17 (2017): 4093–103. http://dx.doi.org/10.1039/c7gc01672g.

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42

Chauhan, M. H., and N. L. Solanki. "Synthesis and Biological Evaluation of Biphenyl Derivatives of Hydrazine via Palladium Catalyzed Suzuki-Miyaura Coupling Reaction." Asian Journal of Organic & Medicinal Chemistry 7, no. 3 (2022): 265–69. http://dx.doi.org/10.14233/ajomc.2022.ajomc-p395.

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Generally, several methods for the construction of biphenyls, including Stille coupling, GombergBachmann reaction, Ullmann reaction and Suzuki-Miyaura cross-coupling are reported. In present research, considering the particularities of these methods and the characteristics of the target compounds by Suzuki-Miyaura cross-coupling reaction. To investigate the optimal conditions, a model reaction was performed using 1-bromo-4-iodobenzene and phenyl boronic acid under different conditions. The products were characterized by FT-IR, mass, 1H NMR and 13C NMR spectroscopy.
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43

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 (August 31, 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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44

Ohtaka, Atsushi. "Transition-metal Nanoparticles Catalyzed Carbon-Carbon Coupling Reactions in Water." Current Organic Chemistry 23, no. 6 (July 4, 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, Sonogashira, Stille, Hiyama, and Ullmann coupling reactions in water.
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45

Ryu, Sang Hyun, Doo Hun Lee, Sang Moon Lee, Hae Jin Kim, Yoon-Joo Ko, Kyoung Chul Ko, and Seung Uk Son. "Morphology engineering of a Suzuki coupling-based microporous organic polymer (MOP) using a Sonogashira coupling-based MOP for enhanced nitrophenol sensing in water." Chemical Communications 55, no. 64 (2019): 9515–18. http://dx.doi.org/10.1039/c9cc05011f.

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46

Carrera Cevallos, Jeanette Verónica, Maribel Cecilila Pérez Pirela, and Ruth Narcisa Pérez Salinas. "Síntesis de complejos de Ni con ligandos carbeno N- Heterocíclico. Aplicación en reacciones de acoplamiento C-C de Suzuki." Alimentos Ciencia e Ingeniería 29, no. 1 (June 30, 2022): 63–79. http://dx.doi.org/10.31243/aci.v29i1.1725.

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Metalodendrymers are very important compounds in the area of catalysis. In the present study, dendritic nickel organometalic compounds with N-heterocyclic carbene ligands are synthesized, using Frechét-type poly (aryl ether) dendrons. The prepared compounds were used to apply them in catalytic processes such as the Suzuki reaction for C-C couplings. The present study proposes the structural analysis of the compounds by spectroscopic and crystalographic techniques, as well as the performance of this type of catalyst in the Suzuki coupling reaction followed by chromatographic techniques, it was concluded that dendritic nickel organometallic compounds with ligands N-heterocyclic carbene are obtained with yields greater than 80%, they present cis-trans isomerism, according to the relative position of the ligands in the square-plane environment of nickel, as well as the syn-anti isomerism due to the slow rotation around to the Ni-C axis and the position of the mesityls located on both carben ligands or on opposite sides of the complex plane. The activity of the catalyst in the Suzuki coupling reaction decreases in the second cycle, despite this it reaches a conversion of 72% in 120 minutes.
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47

de Meijere, Armin, Baldur Stulgies, Karsten Albrecht, Karsten Rauch, Hermann A. Wegner, Henning Hopf, Lawrence T. Scott, Lior Eshdat, Ivan Aprahamian, and Mordecai Rabinovitz. "New interesting molecular topologies by way of modern cross-coupling reactions." Pure and Applied Chemistry 78, no. 4 (January 1, 2006): 813–30. http://dx.doi.org/10.1351/pac200678040813.

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Modern transition-metal-catalyzed cross-coupling reactions, especially of the Kumada, Heck, and Suzuki types, have provided facile access to various bridge-annelated [2.2]paracyclophane derivatives including trifoliaphane and its tribenzo analog. The reduction of trifoliaphane with potassium metal in [D8]-THF led to hexakis[p-benzyl]benzene anion, which could efficiently be trapped with various electrophiles. Highly efficient multifold Suzuki couplings were performed with hexabromobenzene, octabromonaphthalene, and hexabromotriphenylene. The obtained hexa- and octaalkenylarene derivatives disclose interesting molecular shapes. Eventually, a newly developed cascade coupling of bromoarenes containing peri-positioned C-H bonds has led to indeno-annelated polycyclic aromatic hydrocarbons including indenocorannulene as well as the tetrakis- and tris(tert-butylindeno)pyrene which disclose very interesting spectroscopic properties. In particular, tetrakis(tert-butylindeno)pyrene self-assembles in solution by way of π-stacking, and it can be reduced with potassium metal to a stable dianion, a readily dimerizing trianion radical, and a tetraanion.
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48

Tardiff, Bennett J., Joshua C. Smith, Stephen J. Duffy, Christopher M. Vogels, Andreas Decken, and Stephen A. Westcott. "Synthesis, characterization, and reactivity of Pd(II) salicylaldimine complexes derived from aminophenols." Canadian Journal of Chemistry 85, no. 5 (May 1, 2007): 392–99. http://dx.doi.org/10.1139/v07-036.

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Schiff bases, derived from the condensation of salicylaldehydes with 3- and 4-aminophenol, reacted with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalysts for the Suzuki–Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids, using water as a solvent.Key words: cross-coupling, green chemistry, palladium, salicylaldimines, Schiff base, Suzuki–Miyaura.
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Li, Chengxi, Guolan Xiao, Qing Zhao, Huimin Liu, Tao Wang, and Wenjun Tang. "Sterically demanding aryl–alkyl Suzuki–Miyaura coupling." Org. Chem. Front. 1, no. 3 (2014): 225–29. http://dx.doi.org/10.1039/c4qo00024b.

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50

DeShong, Philip, Christopher J. Handy, and Molly E. Mowery. "Hypervalent siloxane derivatives. An alternative to Stille and Suzuki couplings." Pure and Applied Chemistry 72, no. 9 (January 1, 2000): 1655–58. http://dx.doi.org/10.1351/pac200072091655.

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Siloxane methodology is extended to couplings with iodo- and bromoanilines, hindered arylbromides, and substituted siloxanes as substrates. Additionally, initial studies with 5-bromoindole and other heteroaromatics suggest that the siloxane-mediated cross coupling methodology will also be applicable in these systems.
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