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Journal articles on the topic 'Suzuki-Miyaura'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 December 2024

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1

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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2

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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3

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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4

Snieckus, Victor, and Claude Quesnelle. "The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls." Synthesis 50, no. 22 (October 5, 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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5

Onnuch, Polpum, Kranthikumar Ramagonolla, and Richard Y. Liu. "Aminative Suzuki–Miyaura coupling." Science 383, no. 6686 (March 2024): 1019–24. http://dx.doi.org/10.1126/science.adl5359.

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The Suzuki–Miyaura and Buchwald–Hartwig coupling reactions are widely used to form carbon-carbon (C–C) and carbon-nitrogen (C–N) bonds, respectively. We report the incorporation of a formal nitrene insertion process into the Suzuki–Miyaura reaction, altering the products from C–C–linked biaryls to C–N–C–linked diaryl amines and thereby joining the Suzuki–Miyaura and Buchwald–Hartwig coupling pathways to the same starting-material classes. A combination of a bulky ancillary phosphine ligand on palladium and a commercially available amination reagent enables efficient reactivity across aryl halides and pseudohalides, boronic acids and esters, and many functional groups and heterocycles. Mechanistic insights reveal flexibility on the order of bond-forming events, suggesting potential for expansion of the aminative cross-coupling concept to encompass diverse nucleophiles and electrophiles as well as four-component variants.

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6

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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7

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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8

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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9

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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10

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 (December 22, 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 processes, allowing reactions to be performed at low catalyst levels, to prepare extreme 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 processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, also for reactions of aryl chlorides by temperature 100 ºC and pressure 1 atm. Sterically demanding and strongly Lewis-basic ferrocene-based phosphines are water- and oxygen-resistant. The Suzuki–Miyaura reaction is also an important reaction in the ground and fine organic synthesis, in the production of drugs and intermediates. To analyze the conversion of halogen aryl compounds the <sup>1</sup>H NMR spectroscopy was used. The advantage of Suzuki–Miyaura reaction in comparison with other cross-coupling reactions (Kumada-, Heck-, Heck-Carbonylation-, Murahashi-, Sonogashira-, Negishi-, Stille-reaktion, etc.) is in the usage of low toxic, water- and oxygen-insensitive thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. Catalyst, precursor and weak base were dissolved in toluene. All reactions were performed under an atmosphere of nitrogen or argon. The catalytic cycle of Suzuki–Miyaura reaction typically includes three main steps: oxidative addition of the haloaromatic to catalytic active palladium (0) species, transmetalation, and reductive elimination of the product under back formation of catalytically active species. All used catalysts showed good activity with aryl bromides and weak activity with aryl chlorides.</p>

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11

Lan, Yingdong, Jianjun Yuan, Qin Yang, and Yiyuan Peng. "Phosphorus ligand-free Suzuki–Miyaura reactions in the presence of ABTS at room temperature in water." Canadian Journal of Chemistry 99, no. 5 (May 2021): 491–95. http://dx.doi.org/10.1139/cjc-2020-0433.

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A catalytic system for a phosphorus ligand-free Suzuki–Miyaura reaction in water at room temperature was disclosed. Ammonium 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonate) (ABTS) was an efficient promoter and acted both as a ligand and as a surfactant for the synthesis of biaryl compounds via the Suzuki–Miyaura reaction in water. The targeted biaryl architectures were achieved under mild conditions with high efficiency and good functional group tolerance.

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12

Pruschinski, Lucas, Ana-Luiza Lücke, Tyll Freese, Sean-Ray Kahnert, Sebastian Mummel, and Andreas Schmidt. "Suzuki–Miyaura Cross-Couplings under Acidic Conditions." Synthesis 52, no. 06 (November 14, 2019): 882–92. http://dx.doi.org/10.1055/s-0039-1691487.

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Suzuki–Miyaura reactions with Pd(PPh3)4 have been carried out using lithium N-phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki–Miyaura reaction have been examined.

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13

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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14

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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15

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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16

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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17

Golovenko, Ekaterina A., Anastasia N. Kocheva, Artem V. Semenov, Svetlana O. Baykova, Konstantin V. Deriabin, Sergey V. Baykov, Vadim P. Boyarskiy, and Regina M. Islamova. "Palladium-Functionalized Polysiloxane Drop-Casted on Carbon Paper as a Heterogeneous Catalyst for the Suzuki–Miyaura Reaction." Polymers 16, no. 19 (October 6, 2024): 2826. http://dx.doi.org/10.3390/polym16192826.

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In this work, a Pd(II)-C,N-cyclometalated complex was grafted to polysiloxanes via azide–alkyne cycloaddition. The obtained polymer–metal complex (Pd-PDMS) acts as a catalyst in the Suzuki–Miyaura reaction. Pd-PDMS was drop-casted onto a carbon fiber support, and the resulting membrane demonstrated catalytic activity in the cross-coupling reaction without yield loss after several catalytic cycles. The catalytic membrane allows for easy catalyst recycling and provides ultra-low palladium levels in Suzuki–Miyaura reaction products.

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18

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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19

Reimann, Sebastian, Silvio Parpart, Peter Ehlers, Muhammad Sharif, Anke Spannenberg, and Peter Langer. "Synthesis of tetraarylpyridines by chemo-selective Suzuki–Miyaura reactions of 3,5-dibromo-2,6-dichloropyridine." Organic & Biomolecular Chemistry 13, no. 24 (2015): 6832–38. http://dx.doi.org/10.1039/c5ob00866b.

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20

Sharma, Kamaldeep, Manoj Kumar, and Vandana Bhalla. "Aggregates of the pentacenequinone derivative as reactors for the preparation of Ag@Cu2O core–shell NPs: an active photocatalyst for Suzuki and Suzuki type coupling reactions." Chemical Communications 51, no. 63 (2015): 12529–32. http://dx.doi.org/10.1039/c5cc03907j.

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Aggregates of the pentacenequinone derivative stabilized Ag@Cu₂O core–shell nanoparticles (NPs) enabled efficient visible light harvesting to catalyse the palladium free Suzuki–Miyaura and Suzuki type cross coupling reactions at room temperature.

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21

Sherwood, James. "Suzuki–Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents." Beilstein Journal of Organic Chemistry 16 (May 13, 2020): 1001–5. http://dx.doi.org/10.3762/bjoc.16.89.

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The development and study of new solvents has become important due to a proliferation of regulations preventing or limiting the use of many conventional solvents. In this work, the suitability of the Suzuki–Miyaura reaction to demonstrate the usefulness of new solvents was evaluated, including Cyrene™, dimethyl isosorbide, ethyl lactate, 2-methyltetrahydrofuran (2-MeTHF), propylene carbonate, and γ-valerolactone (GVL). It was found that the cross coupling is often unaffected by the choice of solvent, and therefore the Suzuki–Miyaura reaction provides limited information regarding the usefulness of any particular solvent for organic synthesis.

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22

Watson, Allan, Kirsty Wilson, Jane Murray, Helen Sneddon, and Craig Jamieson. "Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions." Synlett 29, no. 17 (September 28, 2018): 2293–97. http://dx.doi.org/10.1055/s-0037-1611054.

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Palladium-catalyzed bond-forming reactions, such as the Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).

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23

Ghosh, Shyamali, William A. Kinney, Diane A. Gauthier, Edward C. Lawson, Tomas Hudlicky, and Bruce E. Maryanoff. "Convenient preparation of aryl-substituted nortropanes by SuzukiMiyaura methodology." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 555–60. http://dx.doi.org/10.1139/v06-045.

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The synthesis of a new bicyclic vinyl boronate (5) was accomplished from N-Boc-nortropinone (6) in two steps. The SuzukiMiyaura coupling of 5 to a variety of aryl bromides and triflates afforded 3-aryl-8-azabicyclo[3.2.1]oct-2-enes in good yields by adjusting the substrate and (or) reaction conditions. Reduction to the 3-aryl-8-azabicyclo[3.2.1]octanes was achieved by hydrogenation. Interestingly, the coupling was also successful with benzyl bromides, providing entry into another group of intermediates.Key words: nortropane, SuzukiMiyaura, boronate, piperidine, GPCR, benzyl bromide.

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24

Zhou, Difei, Nutifafa Y. Doumon, Mustapha Abdu-Aguye, Davide Bartesaghi, Maria A. Loi, L. Jan Anton Koster, Ryan C. Chiechi, and Jan C. Hummelen. "High-quality conjugated polymers via one-pot Suzuki–Miyaura homopolymerization." RSC Advances 7, no. 44 (2017): 27762–69. http://dx.doi.org/10.1039/c7ra03539j.

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25

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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26

Li, Xinmin, Chun Liu, Lei Wang, Qing Ye, Xin Jin, and Zilin Jin. "Temperature-controlled sequential Suzuki–Miyaura reactions for preparing unsymmetrical terphenyls." Organic & Biomolecular Chemistry 16, no. 45 (2018): 8719–23. http://dx.doi.org/10.1039/c8ob01661e.

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27

Yaman, Tolga, and Jeremy N. Harvey. "Suzuki–Miyaura coupling revisited: an integrated computational study." Faraday Discussions 220 (2019): 425–42. http://dx.doi.org/10.1039/c9fd00051h.

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28

Elumalai, Vijayaragavan, and Jørn H. Hansen. "Synthesis of 5,7-diarylindoles via Suzuki–Miyaura coupling in water." Organic & Biomolecular Chemistry 19, no. 47 (2021): 10343–47. http://dx.doi.org/10.1039/d1ob02058g.

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29

West, Matthew J., and Allan J. B. Watson. "Ni vs. Pd in Suzuki–Miyaura sp2–sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system." Organic & Biomolecular Chemistry 17, no. 20 (2019): 5055–59. http://dx.doi.org/10.1039/c9ob00561g.

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30

Li, Zhandong, and Dmitry Kurouski. "Probing the plasmon-driven Suzuki–Miyaura coupling reactions with cargo-TERS towards tailored catalysis." Nanoscale 13, no. 27 (2021): 11793–99. http://dx.doi.org/10.1039/d1nr02478g.

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31

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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32

Tyrol, Chet C., Nang S. Yone, Connor F. Gallin, and Jeffery A. Byers. "Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes." Chemical Communications 56, no. 93 (2020): 14661–64. http://dx.doi.org/10.1039/d0cc05003b.

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33

Hamdy, Aws M., Najim A. Al-Masoudi, Christophe Pannecouque, Qamar Rahman, Alexander Villinger, and Peter Langer. "Regioselective Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modeling study." RSC Advances 5, no. 130 (2015): 107360–69. http://dx.doi.org/10.1039/c5ra16841d.

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34

Laulhé, Sébastien, J. Miles Blackburn, and Jennifer L. Roizen. "Exhaustive Suzuki–Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters." Chemical Communications 53, no. 53 (2017): 7270–73. http://dx.doi.org/10.1039/c7cc00997f.

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35

Labattut, Axel, Ibrahim Abdellah, Julien Buendia, Sandra Abi Fayssal, Erika Adhel, Diana Dragoe, Cyril Martini, Emmanuelle Schulz, and Vincent Huc. "Palladium PEPPSI-IPr Complex Supported on a Calix[8]arene: A New Catalyst for Efficient Suzuki–Miyaura Coupling of Aryl Chlorides." Catalysts 10, no. 9 (September 18, 2020): 1081. http://dx.doi.org/10.3390/catal10091081.

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We report here the synthesis and characterization of a new calix[8]arene-supported PEPPSI-IPr Pd polymetallic complex. This complex, showing greater steric hindrance around the Pd centers compared with previous calix[8]arene-based catalysts, demonstrated high reactivity and selectivity for the Suzuki–Miyaura coupling of aryl chlorides under mild conditions. Along with this good performance, the new catalyst showed low Pd leaching into the final Suzuki–Miyaura coupling products, indicative of a heterogeneous-type reactivity. This rare combination of good reactivity towards challenging substrates and low metal leaching offers great promise at both academic and industrial levels.

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36

Vaaland, Ingrid Caroline, and Magne Olav Sydnes. "Consecutive Palladium Catalyzed Reactions in One-Pot Reactions." Mini-Reviews in Organic Chemistry 17, no. 5 (August 11, 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 used as a catalyst.

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37

Wang, Pei Yu, Guo Heng Zhang, Hai Yan Jiao, and Xiao Ping Zheng. "Palladium Supported on Mesoporous Silica via a Two-Step Method as an Efficient Catalyst for Suzuki-Miyaura Coupling Reactions." Advanced Materials Research 1035 (October 2014): 89–95. http://dx.doi.org/10.4028/www.scientific.net/amr.1035.89.

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In this paper, palladium-containing SBA-15 (Pd/SBA-15) was synthesized via a two-step method. In this procedure, Pd nanoparticles of 3-5 nm in size have been synthesized by formalin reduction method and incorporated into mesoporous SBA-15 silica during hydrothermal synthesis. The resulting nanocomposite with 1.20 wt% Pd loading was achieved with highly dispersed and uniform palladium nanoparticles. The catalytic activity of the Pd/SBA-15 nanocomposite was used as a catalyst for the Suzuki-Miyaura coupling reactions. The Pd/SBA-15 nanocomposite exhibited excellent catalytic activities and reuse ability in air for the Suzuki-Miyaura coupling reactions.

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Sharif, Muhammad, Khurram Shoaib, Shahzad Ahmed, Sebastian Reimann, Jamshed Iqbal, Muhammad Ali Hashmi, Khurshid Ayub, 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 (April 1, 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 reactions of 2,6-dichloro-4-(trifluoromethyl)pyridine with one or two equivalents of arylboronic acids were carried out.

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39

Kadu, Brijesh S. "Suzuki–Miyaura cross coupling reaction: recent advancements in catalysis and organic synthesis." Catalysis Science & Technology 11, no. 4 (2021): 1186–221. http://dx.doi.org/10.1039/d0cy02059a.

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40

Martínez, Alberto, Jamin L. Krinsky, Itziar Peñafiel, Sergio Castillón, Konstantin Loponov, Alexei Lapkin, Cyril Godard, and Carmen Claver. "Heterogenization of Pd–NHC complexes onto a silica support and their application in Suzuki–Miyaura coupling under batch and continuous flow conditions." Catalysis Science & Technology 5, no. 1 (2015): 310–19. http://dx.doi.org/10.1039/c4cy00829d.

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Wood, Alex B., Kakasaheb Y. Nandiwale, Yiming Mo, Bo Jin, Alexander Pomberger, Victor L. Schultz, Fabrice Gallou, Klavs F. Jensen, and Bruce H. Lipshutz. "Continuous flow Suzuki–Miyaura couplings in water under micellar conditions in a CSTR cascade catalyzed by Fe/ppm Pd nanoparticles." Green Chemistry 22, no. 11 (2020): 3441–44. http://dx.doi.org/10.1039/d0gc00378f.

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42

Reizman, Brandon J., Yi-Ming Wang, Stephen L. Buchwald, and Klavs F. Jensen. "Suzuki–Miyaura cross-coupling optimization enabled by automated feedback." Reaction Chemistry & Engineering 1, no. 6 (2016): 658–66. http://dx.doi.org/10.1039/c6re00153j.

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43

Labattut, Axel, Sandra Abi Fayssal, Julien Buendia, Ibrahim Abdellah, Vincent Huc, Cyril Martini, and Emmanuelle Schulz. "Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings." Reaction Chemistry & Engineering 5, no. 8 (2020): 1509–14. http://dx.doi.org/10.1039/d0re00118j.

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44

Damljanović, Ivan, Dragana Stevanović, Anka Pejović, Danijela Ilić, Marija Živković, Jovana Jovanović, Mirjana Vukićević, Goran A. Bogdanović, Niko S. Radulović, and Rastko D. Vukićević. "The palladium(ii) complex of N,N-diethyl-1-ferrocenyl-3-thiabutanamine: synthesis, solution and solid state structure and catalytic activity in Suzuki–Miyaura reaction." RSC Adv. 4, no. 82 (2014): 43792–99. http://dx.doi.org/10.1039/c4ra08140d.

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Yan, Ning, Yujun He, Hui Wen, Fangfang Lai, Dali Yin, and Huaqing Cui. "A Suzuki–Miyaura method for labelling proliferating cells containing incorporated BrdU." Analyst 143, no. 5 (2018): 1224–33. http://dx.doi.org/10.1039/c7an01934c.

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46

Benny, Anjitha Theres, Masthan Thamim, Prakhar Srivastava, Sindoora Suresh, Krishnan Thirumoorthy, Loganathan Rangasamy, Karthikeyan S., Nalini Easwaran, and Ethiraj Kannatt Radhakrishnan. "Synthesis and study of antibiofilm and antivirulence properties of flavonol analogues generated by palladium catalyzed ligand free Suzuki–Miyaura coupling against Pseudomonas aeruginosa PAO1." RSC Advances 14, no. 18 (2024): 12278–93. http://dx.doi.org/10.1039/d3ra08617h.

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47

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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48

Singh, Gurpreet, Manoj Kumar, Kamaldeep Sharma, and Vandana Bhalla. "A supramolecular ensemble of a PBI derivative and Cu2O NPs: potential photocatalysts for the Suzuki and Suzuki type coupling reactions." Green Chemistry 18, no. 11 (2016): 3278–85. http://dx.doi.org/10.1039/c5gc03012a.

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The in situ generated supramolecular ensemble (2:Cu₂O) of Cu₂O NPs and aggregates of PBI derivative 2 exhibited excellent photocatalytic efficiency in the Suzuki–Miyaura and Suzuki type cross-coupling reactions under mild and eco-friendly conditions.

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49

Era, Yuta, Jonathan A. Dennis, Stephen Wallace, and Louise E. Horsfall. "Micellar catalysis of the Suzuki Miyaura reaction using biogenic Pd nanoparticles from Desulfovibrio alaskensis." Green Chemistry 23, no. 22 (2021): 8886–90. http://dx.doi.org/10.1039/d1gc02392f.

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Basnet, Prakash, Surendra Thapa, Diane A. Dickie, and Ramesh Giri. "The copper-catalysed Suzuki–Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation." Chemical Communications 52, no. 74 (2016): 11072–75. http://dx.doi.org/10.1039/c6cc05114f.

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