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Journal articles on the topic 'Ullman coupling reaction'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Baqi, Younis. "Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions." Catalysts 11, no. 1 (2020): 46. http://dx.doi.org/10.3390/catal11010046.

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Cross-coupling reactions furnishing carbon–carbon (C–C) and carbon–heteroatom (C–X) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Ullmann, Ullman–Goldberg, Cadiot–Chodkiewicz, Castro–Stephens, and Corey–House, utilizing elemental copper or its salts as catalyst have, for decades, attracted and inspired scientists. However, these reactions were suffering from the range of functional groups tolerated as well as severely restricted by the harsh reaction conditions often required high temperatures (150–200 °C) for extended reaction time.

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2

Mohammad, Mehdi Khodaei, Alizadeh Abdolhamid, and Haghipour Maryam. "Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe 3 O 4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction." Research on Chemical Intermediates 45 (February 6, 2019): 2727–47. https://doi.org/10.1007/s11164-019-03760-0.

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Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diarylethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.

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3

Waters, Gabrielle D., and Jesse D. Carrick. "Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction." RSC Advances 10, no. 18 (2020): 10807–15. http://dx.doi.org/10.1039/d0ra00673d.

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4

Chang, En-Chiuan, Chun-Yen Chen, Li-Ya Wang, Yu-Ying Huang, Mou-Yung Yeh, and Fung Fuh Wong. "Synthesis of 5-arylamino-1-arylpyrazoles from 5-aminopyrazoles with arylhalides via CuI catalyzed Ullman coupling reaction." Tetrahedron 69, no. 2 (2013): 570–76. http://dx.doi.org/10.1016/j.tet.2012.11.022.

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5

Chang, En-Chiuan, Chun-Yen Chen, Li-Ya Wang, Yu-Ying Huang, Mou-Yung Yeh, and Fung Fuh Wong. "ChemInform Abstract: Synthesis of 5-Arylamino-1-arylpyrazoles from 5-Aminopyrazoles with Arylhalides via CuI Catalyzed Ullman Coupling Reaction." ChemInform 44, no. 23 (2013): no. http://dx.doi.org/10.1002/chin.201323116.

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6

Shaabani, Ahmad, and Ronak Afshari. "Magnetic Ugi-functionalized graphene oxide complexed with copper nanoparticles: Efficient catalyst toward Ullman coupling reaction in deep eutectic solvents." Journal of Colloid and Interface Science 510 (January 2018): 384–94. http://dx.doi.org/10.1016/j.jcis.2017.09.089.

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7

Al-Shboul, Tareq M. A., Suha S. Al-Tarawneh, Taher S. Ababneh, and Taghreed M. A. Jazzazi. "Post-Functionalization of Bromo-Substituted Ether-Linked Polymers via Ullman Coupling Reaction: Synthesis, Characterization and Their Role toward Carbon Dioxide Capture." Separations 9, no. 3 (2022): 55. http://dx.doi.org/10.3390/separations9030055.

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A new open-chain ether-linked polymer has been prepared via nucleophilic aromatic substitution reaction on a C-F bond of 1,4-dibromo-2,5-difluorobenzene by using 2,2-bis(4-hydroxyphenyl) hexafluoropropane (bisphenol AF or BAF). The new polymer (PE-AF) has shown a good solubility in non-polar solvents, good thermal stability (up to 300 °C) and random surface morphology. Tailoring these properties has been achieved by utilizing the post-modification synthetic methodology on the bromo-sites of the polymer backbone via the application of an Ullmann coupling reaction with aniline to form the polyme

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8

O’Driscoll, Luke J., Sissel S. Andersen, Marta V. Solano, et al. "Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes." Beilstein Journal of Organic Chemistry 11 (July 3, 2015): 1112–22. http://dx.doi.org/10.3762/bjoc.11.125.

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The electron-donor and unique redox properties of the tetrathiafulvalene (TTF, 1) moiety have led to diverse applications in many areas of chemistry. Monopyrrolotetrathiafulvalenes (MPTTFs, 4) and bispyrrolotetrathiafulvalenes (BPTTFs, 5) are useful structural motifs and have found widespread use in fields such as supramolecular chemistry and molecular electronics. Protocols enabling the synthesis of functionalised MPTTFs and BPTTFs are therefore of broad interest. Herein, we present the synthesis of a range of functionalised MPTTF and BPTTF species. Firstly, the large-scale preparation of the

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9

Fui, Choong Jian, Mohd Sani Sarjadi, Shaheen M. Sarkar, and Md Lutfor Rahman. "Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst." Catalysts 10, no. 10 (2020): 1103. http://dx.doi.org/10.3390/catal10101103.

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Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, and ligands. Copper catalyst has received great attention owing to the low toxicity and low cost. However, traditional Ullmann-type couplings suffer from limited substrate scopes and harsh reaction conditions. The introduction of homogeneous copper catalyst with presence o

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10

Li, Yuqiang, and Guoyin Yin. "Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp2-Hybridized Organohalides." Synlett 32, no. 16 (2021): 1657–61. http://dx.doi.org/10.1055/a-1608-5693.

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AbstractCross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.

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11

Zhang, Chi, Qiang Sun, Hua Chen, Qinggang Tan, and Wei Xu. "Formation of polyphenyl chains through hierarchical reactions: Ullmann coupling followed by cross-dehydrogenative coupling." Chemical Communications 51, no. 3 (2015): 495–98. http://dx.doi.org/10.1039/c4cc07953a.

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From an interplay of UHV-STM imaging and DFT calculations, we have illustrated on-surface formation of polyphenyl chains through a hierarchical reaction pathway involving two different kinds of reactions (Ullmann coupling and cross-dehydrogenative coupling).

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12

Ribas, Xavi, and Imma Güell. "Cu(I)/Cu(III) catalytic cycle involved in Ullmann-type cross-coupling reactions." Pure and Applied Chemistry 86, no. 3 (2014): 345–60. http://dx.doi.org/10.1515/pac-2013-1104.

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Abstract Copper-catalyzed cross-coupling reactions for C–heteroatom bond formation have attracted numerous research groups in the past 15 years aiming at finding more efficient methodologies under milder conditions. The use of auxiliary ligands has tremendously improved Ullmann-type couplings although a general methodology for different heteroatom-nucleophiles is still lacking. Mechanistic insights are seen as a clue for designing new effective, broad-scope and general methodologies. In this review we describe the widely discussed mechanistic options for this reaction and the use of model comp

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13

Han, Fengyan, Jiawei Xia, Xinglong Zhang, and Yongsheng Fu. "PdAu alloy nanoparticles supported on nitrogen-doped carbon black as highly active catalysts for Ullmann coupling and nitrophenol hydrogenation reactions." RSC Advances 9, no. 31 (2019): 17812–23. http://dx.doi.org/10.1039/c9ra01685f.

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14

Delaney, Connor P., Eva Lin, Qinan Huang, et al. "Cross-coupling by a noncanonical mechanism involving the addition of aryl halide to Cu(II)." Science 381, no. 6662 (2023): 1079–85. http://dx.doi.org/10.1126/science.adi9226.

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Copper complexes are widely used in the synthesis of fine chemicals and materials to catalyze couplings of heteroatom nucleophiles with aryl halides. We show that cross-couplings catalyzed by some of the most active catalysts occur by a mechanism not previously considered. Copper(II) [Cu(II)] complexes of oxalamide ligands catalyze Ullmann coupling to form the C–O bond in aryl ethers by concerted oxidative addition of an aryl halide to Cu(II) to form a high-valent species that is stabilized by radical character on the oxalamide ligand. This mechanism diverges from those involving Cu(I) and Cu(

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15

Wu, Jinsheng, Xiaolong Li, Mingyu Yang, Yujie Gao, Qianru Lv, and Baohua Chen. "Convenient synthesis of ferrocene amines via Cu-catalyzed coupling reaction." Canadian Journal of Chemistry 86, no. 9 (2008): 871–74. http://dx.doi.org/10.1139/v08-096.

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An efficient copper-catalyzed Ullmann-type cross-coupling reaction without ligand of iodo-ferrocene with amines has been reported. In this process, a range of ferrocenyl amine compounds have been prepared in moderate to good yields.Key words: amines, iodo-ferrocene, cross-coupling, copper, Ullmann coupling.

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16

Imrich, Michael R., Jochen Kraft, Cäcilia Maichle-Mössmer, and Thomas Ziegler. "D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation." Beilstein Journal of Organic Chemistry 14 (August 8, 2018): 2082–89. http://dx.doi.org/10.3762/bjoc.14.182.

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Phosphinooxazoline (PHOX) ligands are an important class of ligands in asymmetric catalysis. We synthesized ten novel D-fructose-derived spiro-fused PHOX ligands with different steric and electronic demand. The application of two of them was tested in asymmetric allylic alkylation. The ligands are prepared in two steps from readily available 1,2-O-isopropylidene protected β-D-fructopyranoses by the BF3·OEt2-promoted Ritter reaction with 2-bromobenzonitrile to construct the oxazoline moiety followed by Ullmann coupling of the resulting aryl bromides with diphenylphosphine. Both steps proceeded

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17

Liu, Liqian, Xinrui Miao, Tingting Shi, et al. "Conformation modification of terthiophene during the on-surface synthesis of pure polythiophene." Nanoscale 12, no. 35 (2020): 18096–105. http://dx.doi.org/10.1039/d0nr04529b.

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18

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

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

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19

Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenatio

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20

Lam, Solita, Yvonne Puplampu Dove, Adrienne Morris, Ayunna Epps, and Ghislain R. Mandouma. "Cross-Coupling Biarylation of Nitroaryl Chlorides Through High Speed Ball Milling." International Journal for Innovation Education and Research 3, no. 6 (2015): 12–35. http://dx.doi.org/10.31686/ijier.vol3.iss6.376.

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Solvent-free reaction using a high-speed ball milling technique has been applied to the classical Ullmann coupling reaction. Cross-coupling biarylation of several nitroaryl chlorides was achieved in good yields when performed in custom-made copper vials through continuous shaking without additional copper or solvent. Cross-coupling products were obtained almost pure and NMR-ready. These reactions were cleaner than solution phase coupling which require longer reaction time in high boiling solvents, and added catalysts as well as lengthy extraction and purification steps. Gram quantities of cros

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21

Zhou, Bingwei, Yunkui Liu, Hongwei Jin, and Daohong Liu. "One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines To Access 2,3-Dihydro-1H-imidazo[1,2-a]indoles." Synthesis 52, no. 09 (2020): 1417–24. http://dx.doi.org/10.1055/s-0037-1610739.

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A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C–N bonds are constructed by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

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22

Parvathi Santhoshkumar, C. Rajalakshmi, Lydia Elizabeth Mathews, Rehin Sulay, and Vibin Ipe Thomas. "Mechanistic Views on First-row Earth-Abundant Transition Metal Catalyzed Ullmann-type O-Arylation Reactions." CHIMIA 77, no. 4 (2023): 246. http://dx.doi.org/10.2533/chimia.2023.246.

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Transition metal-catalyzed reactions have attracted much attention in synthetic organic chemistry due to their important role in the formation of C-heteroatom bonds. Ullmann coupling has risen in prominence in recent decades owing to its utilization in the synthesis of biaryl ethers found in a wide range of natural products together with biologically essential molecules, including antibiotics and major industrial polymers. In this article we provide the current understanding of the theoretical aspects of the underlying mechanism of the Ullmann-type O-arylation reaction.

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23

Sherborne, Grant J., Sven Adomeit, Robert Menzel, et al. "Origins of high catalyst loading in copper(i)-catalysed Ullmann–Goldberg C–N coupling reactions." Chemical Science 8, no. 10 (2017): 7203–10. http://dx.doi.org/10.1039/c7sc02859h.

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A mechanistic investigation of Ullmann–Goldberg reactions using common bases led to the identification of pathways for catalyst deactivation. The solid form of the inorganic phase was found to have critical influence on the mechanism of the reaction.

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24

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

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

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25

Cai, Qian, Hui Zhang, Benli Zou, et al. "Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis." Pure and Applied Chemistry 81, no. 2 (2009): 227–34. http://dx.doi.org/10.1351/pac-con-08-08-19.

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Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, either as substrates or ligands, can lead Cu-catalyzed C-N, C-O, C-S, and C-C bond formations work at relatively low temperatures. An ortho-substitution effect caused by NHCOR groups is discussed. Applications of these newly developed reactions to heterocycle preparation and asymmetric synthesis are

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26

Hao, Xiaoyu, Yan Li, Hongyan Ji, et al. "Direct Visualization of Organometallic Intermediates on Cu(111) with Bond-Resolving Non-Contact Atomic Force Microscopy." Surfaces 7, no. 3 (2024): 529–36. http://dx.doi.org/10.3390/surfaces7030035.

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In this study, we investigated the surface-confined coupling reactions of 1,8-dibromobiphenylene (BPBr2) on Cu(111) to elucidate the details of the organometallic intermediates via Ullmann reactions. We used scanning tunneling microscopy (STM) to characterize the resulting organometallic intermediates. Moreover, submolecular resolution of the non-contact atomic force microscopy (nc-AFM) qPlus technique enables the bond-resolving within the organometallic dimer product. Our findings reveal the debromination of BPBr2 on Cu(111), leading to the formation of an organometallic dimer intermediate at

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27

Gopal, Chandra Maity, Kumar Ghosh Ashim, and Kumar Ghosh Pradip. "Green Chemistry: Synthesis of organic compounds through green approach." Journal of Indian Chemical Society Vol. 97, No. 12c, Dec 2020 (2020): 2897–902. https://doi.org/10.5281/zenodo.5654621.

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Department of Chemistry, bDepartment of Physics, Abhedananda Mahavidyalaya, Sainthia, Birbhum-731 234, West Bengal, India <em>E-mail:</em> gcm79@rediffmail.com <em>Manuscript received online 01 December 2020, accepted 22 December 2020</em> Green synthesis of various organic compounds has been done using common organic reactions such as biosynthesis of organic compounds Michael, aldol, Cannizaro reactions, Hoffmann, Wittig, Benzoin, Simon Smith, Heck, Suzuki coupling, Ullmann reaction and aromatic nucleophelic substitution reactions. These names reactions are carried out in green solvents like

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28

Shi, Quanquan, Zhaoxian Qin, Hui Xu, and Gao Li. "Heterogeneous Cross-Coupling over Gold Nanoclusters." Nanomaterials 9, no. 6 (2019): 838. http://dx.doi.org/10.3390/nano9060838.

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Au clusters with the precise numbers of gold atoms, a novel nanogold material, have recently attracted increasing interest in the nanoscience because of very unique and unexpected properties. The unique interaction and electron transfer between gold clusters and reactants make the clusters promising catalysts during organic transformations. The AunLm nanoclusters (where L represents organic ligands and n and m mean the number of gold atoms and ligands, respectively) have been well investigated and developed for selective oxidation, hydrogenation, photo-catalysis, and so on. These gold clusters

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29

Alizadeh, Abdollah, Mohammad A. Khalilzadeh, Eskandar Alipour, and Daryoush Zareyee. "Pd (II) Immobilized on Clinoptilolite as a Highly Active Heterogeneous Catalyst for Ullmann Coupling-type S-arylation of Thiols with Aryl Halides." Combinatorial Chemistry & High Throughput Screening 23, no. 7 (2020): 658–66. http://dx.doi.org/10.2174/1386207323666200415103239.

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Background: There are a number of protocols for Ullmann coupling–type S-arylation reactions, many of them suffer from the use of homogenous and often corrosive catalyst, cumbersome workup procedures, and long reaction times. Besides, many of these reagents are expensive and non-recoverable, leading to the generation of a large amount of toxic waste particularly when large-scale applications are considered. Objective: The aim of this study was to prepare a new Pd catalyst bonded on the surface of zeolite as a heterogeneous catalyst. Methods: A heterogeneous palladium catalyst has been prepared

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30

Gorginpour, Forough, Hassan Zali-Boeini, and Hadi Amiri Rudbari. "A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C–N coupling reaction." RSC Advances 11, no. 6 (2021): 3655–65. http://dx.doi.org/10.1039/d0ra10741g.

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31

Rodríguez-Fernández, Jonathan, Søren Birthin Schmidt, and Jeppe V. Lauritsen. "Sulfur-driven switching of the Ullmann coupling on Au(111)." Chemical Communications 54, no. 29 (2018): 3621–24. http://dx.doi.org/10.1039/c8cc01007b.

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32

Clavé, Guillaume, Claire Garel, Cyril Poullain, et al. "Ullmann reaction through ecocatalysis: insights from bioresource and synthetic potential." RSC Advances 6, no. 64 (2016): 59550–64. http://dx.doi.org/10.1039/c6ra08664k.

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33

Murphy, Colin J., Zachary C. Smith, Alex Pronschinski, et al. "Ullmann coupling mediated assembly of an electrically driven altitudinal molecular rotor." Physical Chemistry Chemical Physics 17, no. 47 (2015): 31931–37. http://dx.doi.org/10.1039/c5cp05294g.

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34

Tajbakhsh, Mahmood, Ali Ramezani, Mohammad Qandalee, et al. "Carbon–Heteroatom Bond Formation via Coupling Reactions Performed on a Magnetic Nanoparticle Bed." AppliedChem 1, no. 2 (2021): 75–89. http://dx.doi.org/10.3390/appliedchem1020007.

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Cross-coupling reactions leading to carbon–heteroatom bonds yield compounds that attract substantial interest due to their role as structural units in many synthetic protocols for bioactive and natural products. Therefore, many research works aim at the improvement of heterogeneous catalytic protocols. We have studied the use of magnetite nanoparticles and solid base compounds in organic synthetic reactions in carbon–heteroatom bond formation because they can be flocculated and dispersed, and reversibly controlled by applying a magnetic field. In this work, we have developed an efficient and s

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35

Ostache, Nicu-Cosmin, Marie-Aude Hiebel, Adriana-Luminiţa Fînaru, Hassan Allouchi, Gérald Guillaumet, and Franck Suzenet. "Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles." RSC Advances 11, no. 16 (2021): 9756–65. http://dx.doi.org/10.1039/d1ra00314c.

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A convenient design of pyrazolo[3,4-c]pyrazoles is reported through hydrazine condensations and C–N Ullmann-type cross-coupling reactions. Chemoselective bromination followed by Suzuki–Miyaura cross-coupling reactions access to a variety of modulated heterobicycles.

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36

Lewis, E. A., M. D. Marcinkowski, C. J. Murphy, et al. "Controlling selectivity in the Ullmann reaction on Cu(111)." Chemical Communications 53, no. 55 (2017): 7816–19. http://dx.doi.org/10.1039/c7cc02901b.

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37

Zhang, Rui, Huaiwei Ding, Xiangling Pu, Zhiping Qian, and Yan Xiao. "Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates." Catalysts 10, no. 11 (2020): 1339. http://dx.doi.org/10.3390/catal10111339.

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The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have

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38

Reggelin, Michael, Matthias Hempe, Lutz Schnellbächer, and Tobias Wiesner. "meta- and para-Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions." Synthesis 28, no. 19 (2017): 4489–99. http://dx.doi.org/10.1055/s-0036-1590824.

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Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino

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39

Ma, Weimin, Jiawei Huang, Chao Li, et al. "One-pot synthesis and property study on thieno[3,2-b]furan compounds." RSC Advances 9, no. 13 (2019): 7123–27. http://dx.doi.org/10.1039/c9ra00796b.

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Based on the regioselective intermolecular Suzuki coupling and subsequent intramolecular Ullmann coupling reactions, one-pot synthesis of benzo[4,5]thieno[3,2-b]benzofurans (BTBFs) has been developed.

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40

Xing, Guolong, Tingting Yan, Saikat Das, Ling Ye, and Kaiqi Ye. "Charged porous organic frameworks bearing heteroatoms with enhanced isosteric enthalpies of gas adsorption." RSC Advances 8, no. 36 (2018): 20434–39. http://dx.doi.org/10.1039/c7ra12860f.

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41

Fu, Meiqin, Dongen Lin, Yuanfu Deng, et al. "Pd-catalyzed tandem homocoupling–aldol–dehydration of ortho-acylphenyl iodides." RSC Adv. 4, no. 45 (2014): 23595–603. http://dx.doi.org/10.1039/c4ra02055c.

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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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Wang, Zheng-Jun, Xia Wang, Jing-Jing Lv, et al. "Bimetallic Au–Pd nanochain networks: facile synthesis and promising application in biaryl synthesis." New Journal of Chemistry 41, no. 10 (2017): 3894–99. http://dx.doi.org/10.1039/c7nj00998d.

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

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

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Fischer, Carolin, and Burkhard Koenig. "Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds." Beilstein Journal of Organic Chemistry 7 (January 14, 2011): 59–74. http://dx.doi.org/10.3762/bjoc.7.10.

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N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three mai

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Mastalir, Ágnes, and Árpád Molnár. "A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems." Molecules 28, no. 4 (2023): 1769. http://dx.doi.org/10.3390/molecules28041769.

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The Ullmann reaction has been reported to be the first cross-coupling reaction performed by using a transition metal catalyst. This reaction has been initially considered as the copper-catalyzed homocoupling of aryl halides, leading to the formation of symmetrical biaryl compounds via the generation of novel C–C bonds. Although this reaction has been extensively studied in recent decades and valuable results have been achieved, there are still considerable efforts focused on the development of novel catalytic systems, mild reaction conditions, and extended substrate scope. The mechanistic aspe

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Ge, Xin, Xinzhi Chen, Chao Qian, and Shaodong Zhou. "Efficient Ullmann C–N coupling catalyzed by a recoverable oligose-supported copper complex." RSC Advances 6, no. 64 (2016): 58898–906. http://dx.doi.org/10.1039/c6ra13536f.

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Ge, Xin, Xinzhi Chen, Chao Qian, and Shaodong Zhou. "Combined experimental/theoretical study of d-glucosamine promoted Ullmann-type C–N coupling catalyzed by copper(i): does amino really count?" RSC Advances 6, no. 35 (2016): 29638–45. http://dx.doi.org/10.1039/c6ra03015g.

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Liu, Xuemin, Shuo Chang, Xinzhi Chen, Xin Ge, and Chao Qian. "Efficient Ullmann C–X coupling reaction catalyzed by a recoverable functionalized-chitosan supported copper complex." New Journal of Chemistry 42, no. 19 (2018): 16013–20. http://dx.doi.org/10.1039/c8nj02677g.

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Tang, Cheng, Wenwen Yang, Zhijuan Zou, Fang Liao, Chunmei Zeng, and Kunpeng Song. "Facile Synthesis Hyper-Crosslinked PdFe Bimetallic Polymer as Highly Active Catalyst for Ullmann Coupling Reaction of Chlorobenzene." Polymers 15, no. 12 (2023): 2748. http://dx.doi.org/10.3390/polym15122748.

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The synthesis of efficient and sustainable heterogeneous Pd-based catalysts has been an active field of research due to their crucial role in carbon–carbon coupling reactions. In this study, we developed a facile and eco-friendly in situ assembly technique to produce a PdFe bimetallic hyper-crosslinked polymer (HCP@Pd/Fe) to use as a highly active and durable catalyst in the Ullmann reaction. The HCP@Pd/Fe catalyst exhibits a hierarchical pore structure, high specific surface area, and uniform distribution of active sites, which promote catalytic activity and stability. Under mild conditions,

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