{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T00:41:20Z","timestamp":1792456880199,"version":"4.5.0"},"reference-count":87,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,13]],"date-time":"2023-02-13T00:00:00Z","timestamp":1676246400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2013C 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 aspects of the Ullmann homocoupling reaction have also been investigated, as related to the introduction of new sustainable strategies and green procedures. The application of recyclable heterogeneous catalysts has been found to overcome most of the limitations associated with the harsh reaction conditions of the original Ullmann reaction. More recently, copper-based catalytic systems have also been replaced by palladium nanoparticles, ionic palladium species, gold nanoparticles, and palladium\u2013gold bimetallic systems. In this review, current results reported on the Ullmann homocoupling reaction are discussed, with an emphasis on the development of novel catalytic systems, which can be efficiently used under heterogeneous conditions.<\/jats:p>","DOI":"10.3390\/molecules28041769","type":"journal-article","created":{"date-parts":[[2023,2,14]],"date-time":"2023-02-14T01:41:06Z","timestamp":1676338866000},"page":"1769","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8038-4635","authenticated-orcid":false,"given":"\u00c1gnes","family":"Mastalir","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, University of Szeged, H-6720 Szeged, D\u00f3m t\u00e9r 8, 6720 Szeged, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u00c1rp\u00e1d","family":"Moln\u00e1r","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Szeged, H-6720 Szeged, D\u00f3m t\u00e9r 8, 6720 Szeged, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Baqi, Y. (2021). Recent Advances in microwave-assisted copper-catalyzed cross-coupling reactions. Catalysts, 11.","DOI":"10.3390\/catal11010046"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"793","DOI":"10.1021\/jacs.7b11853","article-title":"Mechanism of the Ullmann biaryl ether synthesis catalyzed by complexes of anionic ligands: Evidence for the reaction of iodoarenes with ligated anionic CuI intermediates","volume":"140","author":"Giri","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Salih, K.S.M., and Baqi, Y. (2020). Microwave-assisted palladium-catalyzed cross-coupling reactions: Generation of carbon\u2013carbon bond. Catalysts, 10.","DOI":"10.3390\/catal10010004"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2474","DOI":"10.1038\/nprot.2007.364","article-title":"Cu-catalyzed Goldberg and Ullmann reactions of aryl halides using chelating N-and O-based ligands","volume":"2","author":"Altman","year":"2007","journal-title":"Nat. Protoc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1865","DOI":"10.1016\/j.tet.2019.02.001","article-title":"Synthesis of symmetrical biaryl compounds by homocoupling reaction","volume":"75","author":"Vasconcelos","year":"2019","journal-title":"Tetrahedron"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2174","DOI":"10.1002\/cber.190103402141","article-title":"\u00dcber Synthesen in der Biphenylreihe","volume":"34","author":"Ullmann","year":"1901","journal-title":"J. Ber. Dtsch. Chem. Ges."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1002\/slct.201803144","article-title":"Ligand-free Cu-catalyzed Suzuki coupling of alkynyl bromides with boronic acids in ethanol under microwave irradiation","volume":"4","author":"Babu","year":"2019","journal-title":"ChemistrySelect"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3054","DOI":"10.1021\/cr8002505","article-title":"Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis","volume":"108","author":"Evano","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1359","DOI":"10.1021\/cr000664r","article-title":"Aryl\u2013aryl bond formation one century after the discovery of the Ullmann reaction","volume":"102","author":"Hassan","year":"2002","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"10338","DOI":"10.1039\/c0dt00674b","article-title":"The mechanism of the modified Ullmann reaction","volume":"39","author":"Sperotto","year":"2010","journal-title":"Dalton Trans."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5497","DOI":"10.1021\/acs.organomet.5b00567","article-title":"Reactions of the 21st century: Two decades of innovative catalyst design for palladium-catalyzed cross-couplings","volume":"34","author":"Gildner","year":"2015","journal-title":"Organometallics"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1002\/cjoc.202000075","article-title":"Ullmann-Ma reaction: Development, scope and applications in organic synthesis","volume":"38","author":"Cai","year":"2020","journal-title":"Chin. J. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"16136","DOI":"10.1002\/anie.201701690","article-title":"Selected copper-based reactions for C\u2013N, C\u2013O, C\u2013S, and C\u2013C bond formation","volume":"56","author":"Bhunia","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3525","DOI":"10.1039\/C3CS60289C","article-title":"Copper-catalysed Ullmann type chemistry: From mechanistic aspects to modern development","volume":"43","author":"Sambiagio","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2337","DOI":"10.1016\/j.ccr.2004.09.014","article-title":"Copper in cross-coupling reactions: The post-Ullmann chemistry","volume":"248","author":"Beletskaya","year":"2004","journal-title":"Coord. Chem. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1002\/ejoc.201600540","article-title":"Emergence of copper-mediated formation of C\u2013C bonds","volume":"2","author":"Maaliki","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"7275","DOI":"10.1007\/s11696-022-02424-5","article-title":"Recent green synthetic approaches toward Ullmann reaction: A review","volume":"76","author":"Akhtar","year":"2022","journal-title":"Chem. Papers"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"19125","DOI":"10.1039\/C8RA02818D","article-title":"Diaryl ethers synthesis: Nano-catalysts in carbon-oxygen cross-coupling reactions","volume":"8","author":"Nejati","year":"2018","journal-title":"RSC Adv."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Shi, Q., Qin, Z., Xu, H., and Li, G. (2019). Heterogeneous cross-coupling over gold nanoclusters. Nanomaterials, 9.","DOI":"10.3390\/nano9060838"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1007\/s11030-020-10170-7","article-title":"Layered double hydroxides as heterogeneous catalyst systems ih the cross-coupling reactions: An overview","volume":"26","author":"Heravi","year":"2022","journal-title":"Mol. Diversity"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"26097","DOI":"10.1039\/C5RA02468D","article-title":"Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions","volume":"5","author":"McAfee","year":"2015","journal-title":"RSC Adv."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Mpungose, P.P., Vundla, Z.P., Maguire, G.E., and Friedrich, H.B. (2018). The current status of heterogeneous palladium catalysed Heck and Suzuki cross-coupling reactions. Molecules, 23.","DOI":"10.3390\/molecules23071676"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5400","DOI":"10.1002\/anie.200300594","article-title":"Modern synthetic methods for copper-mediated C(aryl) \u2013O, C(aryl)\u2013N, and C(aryl)\u2013S bond formation","volume":"42","author":"Ley","year":"2003","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"110650","DOI":"10.1016\/j.mcat.2019.110650","article-title":"CuO-grafted triazine functionalized covalent organic framework as an efficient catalyst for C-C homo coupling reaction","volume":"480","author":"Das","year":"2020","journal-title":"Mol. Catal."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2600","DOI":"10.3762\/bjoc.11.280","article-title":"Recent advances in copper-catalyzed asymmetric coupling reactions","volume":"11","author":"Zhou","year":"2015","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"7628","DOI":"10.1021\/jo971722k","article-title":"Studies relevant to ellagitannin chemistry: Highly diastereoselective intramolecular biaryl coupling in bis(iodotrimethoxybenzoyl) hexopyranose derivatives","volume":"63","author":"Dai","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1483","DOI":"10.1021\/ol060484p","article-title":"Diastereospecific intramolecular Ullmann couplings: Unique chiral auxiliary for the preparation of 3,3\u2019-disubstituted MeO-BIPHEP derivatives","volume":"8","author":"Gorobets","year":"2006","journal-title":"Org. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1039\/D1RE00054C","article-title":"Synthesis of sub-nanometric Cu2O catalysts for Pd-free C-C coupling reactions","volume":"6","author":"Agrawal","year":"2021","journal-title":"React. Chem. Eng."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1006\/jcat.1998.1979","article-title":"The stability of chromium in CrAPO-5, CrAPO-11, and CrS-1 during liquid phase oxidations","volume":"175","author":"Lempers","year":"1998","journal-title":"J. Catal."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/j.catcom.2017.09.005","article-title":"Fabrication of silica nanoparticle-supported copper quantum dots and the efficient catalytic Ullmann coupling reaction","volume":"102","author":"Gao","year":"2017","journal-title":"Catal. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/0021-9797(68)90272-5","article-title":"Controlled growth of monodisperse silica spheres in the micron size range","volume":"26","author":"Fink","year":"1968","journal-title":"J. Colloid Interf. Sci."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"8561","DOI":"10.1038\/ncomms9561","article-title":"High catalytic activity of oriented 2.0.0. copper(I) oxide grown on graphene film","volume":"6","author":"Primo","year":"2015","journal-title":"Nature Comm."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"9254","DOI":"10.1039\/c2cc34978g","article-title":"From biomass wastes to large-area, high-quality, N-doped graphene: Catalyst-free carbonization of chitosan coatings on arbitrary substrates","volume":"48","author":"Primo","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"15964","DOI":"10.1021\/ja064068b","article-title":"Catalytic C\u2013C bond formation accomplished by selective C\u2013F activation of perfluorinated arenes","volume":"128","author":"Schaub","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"802","DOI":"10.1002\/ajoc.201800041","article-title":"Palladium immobilized onto functionalized magnetic nanoparticles as robust catalysts for amination and room-temperature Ullmann homocoupling of aryl halides: A walk around the C\u2013F bond activation","volume":"7","author":"Moghadamm","year":"2018","journal-title":"Asian J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"e4675","DOI":"10.1002\/aoc.4675","article-title":"Synergistic activities in the Ullmann coupling of chloroarenes at ambient temperature by Pd-supported calcined ferrocenated La2O3","volume":"33","author":"Chumkaeo","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"122","DOI":"10.1016\/j.cattod.2014.03.074","article-title":"Immobilization of Pd(II) on MOFs as a highly active heterogeneous catalyst for Suzuki-Miyaura and Ullmann-type coupling reactions","volume":"245","author":"Chen","year":"2015","journal-title":"Catal. Today"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"995","DOI":"10.1039\/C8GC03862G","article-title":"Ligand free palladium catalyzed Ullmann biaryl synthesis: \u2019household\u2019 reagents and mild reaction conditions","volume":"21","author":"Gong","year":"2019","journal-title":"Green Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"e6613","DOI":"10.1002\/aoc.6613","article-title":"Highly dispersed palladium nanoparticles supported on graphitic carbon nitride for selective hydrogenation of nitro compounds and Ullmann coupling reaction","volume":"36","author":"Bhowmik","year":"2022","journal-title":"Appl. Organomet. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2629","DOI":"10.1055\/s-0033-1339877","article-title":"Site-selective heterofunctionalization of cyclodextrins: Discovery, development and use in catalysis","volume":"24","author":"Sollogoub","year":"2013","journal-title":"Synlett"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"6652","DOI":"10.1039\/C4RA14323J","article-title":"Palladium nanoparticles on \u03b2-cyclodextrin functionalised graphene nanosheets: A supramolecular based heterogeneous catalyst for C-C coupling reactions under green reaction conditions","volume":"5","author":"Putta","year":"2015","journal-title":"RSC Adv."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1021\/ja00106a036","article-title":"Supported monolayers containing preformed binding sites. Synthesis and interfacial binding properties of a thiolated beta-cyclodextrin derivative","volume":"117","author":"Rojas","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"e4608","DOI":"10.1002\/aoc.4608","article-title":"The \u03b2-cyclodextrin decorated with palladium nanoparticles without pretreatment: An efficient heterogeneous catalyst for biaryls synthesis","volume":"32","author":"Feiz","year":"2018","journal-title":"Appl. Organomet. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1021\/jp1084982","article-title":"Tuning the size, the shape and the magnetic properties of iron oxide nanoparticles","volume":"115","author":"Guardia","year":"2011","journal-title":"J. Phys. Chem. C"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3036","DOI":"10.1021\/cr100230z","article-title":"Magnetically recoverable nanocatalysts","volume":"111","author":"Polshettiwar","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"6949","DOI":"10.1021\/cr500134h","article-title":"Fast-growing field of magnetically recyclable nanocatalysts","volume":"114","author":"Wang","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"e5570","DOI":"10.1002\/aoc.5570","article-title":"A bio-inspired magnetically recoverable palladium nanocatalyst for the Ullmann coupling reaction of aryl halides and arylboronic acids in aqueous media","volume":"34","author":"Dubey","year":"2020","journal-title":"Appl. Organomet. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"14283","DOI":"10.1021\/acssuschemeng.8b02940","article-title":"Cu(II) glucose: Sustainable catalyst for the synthesis of quinazolinones in a biomass-derived solvent 2-methylTHF and application for the synthesis of diproqualone","volume":"6","author":"Dubey","year":"2018","journal-title":"ACS Sustainable Chem. Eng."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/j.apcata.2014.09.045","article-title":"Palladium nanoparticle decorated high nitrogen-doped graphene with high catalytic activity for Suzuki-Miyaura and Ullmann type coupling reactions in aqueous media","volume":"488","author":"Movahed","year":"2014","journal-title":"Appl. Catal. A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1339","DOI":"10.1021\/ja01539a017","article-title":"Preparation of graphitic oxide","volume":"80","author":"Offemann","year":"1958","journal-title":"J. Am. Chem. Soc."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"7826","DOI":"10.1021\/la301232r","article-title":"Effect of nitrogen doping on hydrogen storage capacity of palladium decorated graphene","volume":"28","author":"Parambhath","year":"2012","journal-title":"Langmuir"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1002\/cctc.201300893","article-title":"Palladium on ionic liquid derived nanofibrillated mesoporous carbon: A recyclable catalyst for the Ullmann homocoupling reactions of aryl halides in water","volume":"6","author":"Karimi","year":"2014","journal-title":"ChemCatChem"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"8634","DOI":"10.1002\/chem.201200373","article-title":"A Nano-Fibrillated Mesoporous Carbon as an Effective Support for Palladium Nanoparticles in the Aerobic Oxidation of Alcohols \u201con Pure Water\u201d","volume":"18","author":"Karimi","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.jorganchem.2017.11.016","article-title":"Catalytic specificity of linear polystyrene-stabilized Pd nanoparticles during Ullmann coupling reaction in water and the associated mechanism","volume":"854","author":"Ohtaka","year":"2018","journal-title":"J. Organomet. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1021\/ar040062k","article-title":"Some novel polymeric nanocomposites","volume":"39","author":"Mark","year":"2006","journal-title":"Acc. Chem. Res."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/S0928-4931(98)00049-6","article-title":"Formation of noble metal nanoparticles within a polymeric matrix: Nanoparticle features and overall morphologies","volume":"6","author":"Mayer","year":"1998","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2013","DOI":"10.1007\/s11696-018-0421-y","article-title":"Pd-poly(N-vinyl-2-pyrrolidone)\/MCM-48 nanocomposite: A novel catalyst for the Ullmann reaction","volume":"72","author":"Mosaddegh","year":"2018","journal-title":"Chem. Papers"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3286","DOI":"10.1002\/cctc.201402483","article-title":"Immobilized transition metals as catalysts for cross-couplings in continuous flow\u2014A critical assessment of the reaction mechanism and metal leaching","volume":"6","author":"Cantillo","year":"2014","journal-title":"ChemCatChem"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"32719","DOI":"10.1038\/srep32719","article-title":"Continuous flow room temperature reductive aqueous homo-coupling of aryl halides using supported Pd catalysts","volume":"6","author":"Feiz","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3736","DOI":"10.1002\/adsc.201600704","article-title":"Ligand-free Heck reactions of aryl iodides: Significant acceleration of the rate through visible light irradiation at ambient temperature","volume":"358","author":"Zhang","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1725","DOI":"10.1021\/cs5000284","article-title":"Visible light-driven cross-coupling reactions at lower temperatures using a photocatalyst of palladium and gold alloy nanoparticles","volume":"4","author":"Xiao","year":"2014","journal-title":"ACS Catal."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.catcom.2018.03.026","article-title":"Enhancement of Suzuki-Miyaura coupling reaction by photocatalytic palladium nanoparticles anchored to TiO2 under visible light irradiation","volume":"111","author":"Koohgard","year":"2018","journal-title":"Catal. Commun."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1595","DOI":"10.1007\/s10562-019-02749-z","article-title":"Band gap modification of TiO2 nanoparticles by ascorbic acid-stabilized Pd nanoparticles for photocatalytic Suzuki-Miyaura and Ullmann coupling reactions","volume":"149","author":"Feizpour","year":"2019","journal-title":"Catal. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"12322","DOI":"10.1002\/anie.201306769","article-title":"Threefold cross-linked polystyrene-triphenylphosphane hybrids: Mono-P-ligating behavior and catalytic applications of aryl chloride cross-coupling and C(sp3)\u2013H borylation","volume":"52","author":"Iwai","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"2230","DOI":"10.1002\/cctc.201500356","article-title":"Functionalized magnetic mesoporous silica nanoparticle-supported palladium catalysts for carbonylative Sonogashira coupling reactions of aryl iodides","volume":"7","author":"Natour","year":"2015","journal-title":"ChemCatChem"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"8363","DOI":"10.1002\/anie.201103224","article-title":"Palladium-catalyzed borylation of sterically demanding aryl halides with a silica-supported compact phosphane ligand","volume":"50","author":"Kawamorita","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2410","DOI":"10.1016\/j.ccr.2008.06.013","article-title":"Linkers and catalysts immobilized on oxide supports: New insights by solid-state NMR spectroscopy","volume":"252","year":"2008","journal-title":"Coord. Chem. Rev."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"3374","DOI":"10.1002\/ejic.201800291","article-title":"Immobilization of an aminobisphosphine\u2013PdII complex over graphene-oxide: An efficient and reusable catalyst for Suzuki\u2013Miyaura, Ullmann coupling and cyanation reactions","volume":"29","author":"Sengupta","year":"2018","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Karimi, B., and Akhavan, P.F. (2009). Main-chain NHC-palladium polymer as a recyclable self-supported catalyst in the Suzuki-Miyaura coupling of aryl chlorides in water. Chem. Commun., 3750\u20133752.","DOI":"10.1039\/b902096a"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"7686","DOI":"10.1039\/c1cc00017a","article-title":"A novel water-soluble NHC-Pd polymer: An efficient and recyclable catalyst for the Suzuki coupling of aryl chlorides in water at room temperature","volume":"47","author":"Karimi","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"2248","DOI":"10.1002\/cctc.201500383","article-title":"N-Heterocyclic carbene\u2013Pd polymers as reusable precatalysts for cyanation and Ullmann homocoupling of aryl halides: The role of solvent in product distribution","volume":"7","author":"Karimi","year":"2015","journal-title":"ChemCatChem"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3784","DOI":"10.1039\/c2cc30975k","article-title":"Surfactant-free single-nano-sized colloidal Cu nanoparticles for use as an active catalyst in Ullmann-coupling reaction","volume":"48","author":"Isomura","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"5926","DOI":"10.1021\/la9038842","article-title":"Stability of the DMF-protected Au nanoclusters: Photochemical, dispersion, and thermal properties","volume":"26","author":"Kawasaki","year":"2010","journal-title":"Langmuir"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"15752","DOI":"10.1039\/C4DT01856G","article-title":"Synthesis of DMF-protected Au NPs with different size distributions and their catalytic performance in the Ullmann homocoupling of aryl iodides","volume":"43","author":"Jao","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2777","DOI":"10.1002\/adsc.201200422","article-title":"Ullmann homocoupling catalysed by gold nanoparticles in water and ionic liquid","volume":"354","author":"Monopoli","year":"2012","journal-title":"Adv.Synth. Catal."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.3866\/PKU.WHXB201704101","article-title":"A critical review on carbon-carbon coupling over ultra-small gold nanoclusters","volume":"33","author":"Zhou","year":"2017","journal-title":"Acta Phys. Chim. Sin."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1007\/s13738-017-1050-z","article-title":"Ullmann homocoupling of aryl iodides catalyzed by gold nanoparticles stabilized on magnetic mesoporous silica","volume":"14","author":"Rostamizadeh","year":"2017","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/j.catcom.2014.07.029","article-title":"Au anchored to (\u03b1-Fe2O3)-MCM-41-HS as a novel magnetic nanocatalyst for water-medium and solvent-free alkyne hydration","volume":"57","author":"Rostamizadeh","year":"2014","journal-title":"Catal. Commun."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.poly.2016.09.052","article-title":"Cu\u2013Fe layered double hydroxide derived mixed metal oxide: Environmentally benign catalyst for Ullmann coupling of aryl halides","volume":"120","author":"Dumbre","year":"2016","journal-title":"Polyhedron"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.apcata.2014.02.015","article-title":"Mesoporous, ligand-free Cu-Fe solid catalyst mediated CS cross coupling of thiols with aryl halides","volume":"476","author":"Dumbre","year":"2014","journal-title":"Appl. Catal. A"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1002\/cssc.201402718","article-title":"Chitosan as a sustainable organocatalyst: A concise overview","volume":"8","year":"2015","journal-title":"ChemSusChem"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1016\/j.ijbiomac.2017.07.081","article-title":"Co-immobilization of Pd and Zn nanoparticles in chitosan\/silica membranes for efficient, recyclable catalysts used in Ullmann reaction","volume":"105","author":"Liu","year":"2017","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"977","DOI":"10.1002\/anie.199009771","article-title":"The directed synthesis of biaryl compounds: Modern concepts and strategies","volume":"29","author":"Bringmann","year":"1990","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1021\/cr0505674","article-title":"Carbon\u2013carbon coupling reactions catalyzed by heterogeneous palladium catalysts","volume":"107","author":"Yin","year":"2007","journal-title":"J. Chem. Rev."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"6222","DOI":"10.1021\/jp210555s","article-title":"Bimetallic Au\u2013Pd alloy catalysts for N2O decomposition: Effects of surface structures on catalytic activity","volume":"116","author":"Wei","year":"2012","journal-title":"J. Phys. Chem. C"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"1546","DOI":"10.1021\/cs500071c","article-title":"Efficient and durable Au alloyed Pd single-atom catalyst for the Ullmann reaction of aryl chlorides in water","volume":"4","author":"Zhang","year":"2014","journal-title":"ACS Catal."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"7155","DOI":"10.1039\/C8CC00475G","article-title":"Au\u2013Pd bimetallic nanoparticles supported on a high nitrogen-rich ordered mesoporous carbon as an efficient catalyst for room temperature Ullmann coupling of aryl chlorides in aqueous media","volume":"54","author":"Karimi","year":"2018","journal-title":"Chem. Commun."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1769\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:33:48Z","timestamp":1760121228000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1769"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,13]]},"references-count":87,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28041769"],"URL":"https:\/\/doi.org\/10.3390\/molecules28041769","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,13]]}}}