{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T21:04:53Z","timestamp":1790715893458,"version":"4.1.0"},"reference-count":23,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2019,10,12]],"date-time":"2019-10-12T00:00:00Z","timestamp":1570838400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Liaoning Provincial Natural Science Foundation of China","award":["2019-BS-102"],"award-info":[{"award-number":["2019-BS-102"]}]},{"name":"College Students Innovation Training Program of Liaoning Province","award":["201910160017"],"award-info":[{"award-number":["201910160017"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This is the first report of a natural ligand improving the copper-catalyzed homocouplings of (hetero)arylboronic acids. Various important synthetic biaryl intermediates in organic synthesis could be assembled via this method. To gain insight into this reaction, in situ React IR technology was used to confirm the effectivity of this catalyst system. This protocol could provide important biaryl compounds in high yields within a short time.<\/jats:p>","DOI":"10.3390\/molecules24203678","type":"journal-article","created":{"date-parts":[[2019,10,14]],"date-time":"2019-10-14T03:54:13Z","timestamp":1571025253000},"page":"3678","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Cu(II)-Catalyzed Homocouplings of (Hetero)Arylboronic Acids with the Assistance of 2-O-Methyl-d-Glucopyranose"],"prefix":"10.3390","volume":"24","author":[{"given":"Chunling","family":"Yuan","sequence":"first","affiliation":[{"name":"Department of Medicinal Chemistry, Pharmacy School, Jinzhou Medical University, Jinzhou 121001, Liaoning, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Li","family":"Zheng","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry, Pharmacy School, Jinzhou Medical University, Jinzhou 121001, Liaoning, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yingdai","family":"Zhao","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry, Pharmacy School, Jinzhou Medical University, Jinzhou 121001, Liaoning, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,10,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1856","DOI":"10.1021\/jo00111a052","article-title":"Synthesis of (\u2212)-monoterpenylmagnolol and magnolol","volume":"60","author":"Agharahimi","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5272","DOI":"10.1016\/j.bmcl.2008.08.050","article-title":"Synthesis of unsymmetrical biphenyls as potent cytotoxic agents","volume":"18","author":"Wu","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1002\/cber.190403701141","article-title":"Ueber eine neue Darstellungsweise von Phenyl\u00e4thersalicyls\u00e4ure","volume":"37","author":"Ullmann","year":"1904","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6110","DOI":"10.1021\/jo0608063","article-title":"Efficient construction of biaryls and macrocyclic cyclophanes via electron-transfer oxidation of lipshutz cuprates","volume":"71","author":"Miyake","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"6637","DOI":"10.1021\/jo060673l","article-title":"Iron-catalyzed homocoupling of bromide compounds","volume":"71","author":"Xu","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/j.catcom.2007.05.008","article-title":"Pd (OAc) 2-catalyzed room temperature homocoupling reaction of arylboronic acids under air without ligand","volume":"9","author":"Xu","year":"2008","journal-title":"Catal. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"13788","DOI":"10.1021\/ja075417k","article-title":"Manganese- or iron-catalyzed homocoupling of grignard reagents using atmospheric oxygen as an oxidant","volume":"129","author":"Cahiez","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7687","DOI":"10.1016\/j.tetlet.2007.08.083","article-title":"Palladium-catalyzed homocoupling of arenediazonium salts: An operationally simple synthesis of symmetrical biaryls","volume":"48","author":"Robinson","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1735","DOI":"10.1055\/s-0036-1591602","article-title":"Efficient homocoupling of aryl- and alkenylboronic acids in the presence of low loadings of [{Pd (\u03bc-OH) Cl (IPr)} 2]","volume":"29","author":"Ostrowska","year":"2018","journal-title":"Synlett"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3933","DOI":"10.1002\/cctc.201900556","article-title":"Aerobic homocoupling of arylboronic acids catalyzed by regenerable Pd (II) @MIL-88B-NH 2 (Cr)","volume":"11","author":"Valiente","year":"2019","journal-title":"ChemCatChem"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"10130","DOI":"10.1021\/jo034680a","article-title":"Role of copper species in the oxidative dimerization of arylboronic acids:\u2009 Synthesis of symmetrical biaryls","volume":"68","author":"Demir","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1864","DOI":"10.1002\/ejoc.200900173","article-title":"Homocoupling of arylboronic acids catalyzed by 1, 10-phenanthroline-ligated copper complexes in air","volume":"12","author":"Kirai","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6332","DOI":"10.1021\/acs.inorgchem.6b01115","article-title":"Ruthenium-catalyzed oxidative homocoupling of arylboronic acids in water: Ligand tuned reactivity and mechanistic study","volume":"55","author":"Tyagi","year":"2016","journal-title":"Inorg. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6656","DOI":"10.1002\/ejoc.201100994","article-title":"Cu-II\u2013\u03b2-cyclodextrin complex as a nanocatalyst for the homo- and crosscoupling of arylboronic acids under ligand-and base-free conditions in air: Chemoselective cross-coupling of arylboronic acids in water","volume":"2011","author":"Kaboudin","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2266","DOI":"10.1039\/c3gc40753e","article-title":"Fe3O4 nanoparticle-supported Cu(II)-\u03b2-cyclodextrin complex as a magnetically recoverable and reusable catalyst for the synthesis of symmetrical biaryls and 1,2,3-triazoles from aryl boronic acids","volume":"15","author":"Kaboudin","year":"2013","journal-title":"Green Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1317","DOI":"10.1039\/c1gc15045f","article-title":"Triazine functionalized ordered mesoporous polymer: A novel solid support for Pd-mediated C-C cross-coupling reactions in water","volume":"13","author":"Modak","year":"2011","journal-title":"Green Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1293","DOI":"10.1016\/S0040-4039(00)80280-4","article-title":"Coupling of aryl Grignard reagents by electron transfer to 2,3-dichloropropene","volume":"29","author":"Cheng","year":"1988","journal-title":"Tetrahedron Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1039\/C0GC00780C","article-title":"An efficient and recyclable heterogeneous palladiumcatalyst utilizing naturally abundant pearl shell waste","volume":"13","author":"Zeng","year":"2011","journal-title":"Green Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6393","DOI":"10.1021\/ja00387a040","article-title":"Acid-catalyzed solvolysis of N-sulfonyl- and N-acyl-O-arylhydroxylamines. Phenoxenium ions","volume":"104","author":"Endo","year":"1982","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1021\/jo01153a023","article-title":"The chemistry of o-terphenyl. III. Sulfonic acids","volume":"14","author":"Allen","year":"1949","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1680","DOI":"10.1021\/ja01611a086","article-title":"Some tetraorganosilanes","volume":"77","author":"Gilman","year":"1955","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4302","DOI":"10.1016\/j.tetlet.2008.04.123","article-title":"Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd (OAc) 2 using indium","volume":"49","author":"Lee","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9946","DOI":"10.1021\/jo202037x","article-title":"Ni(COD)2\/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature","volume":"76","author":"Leowanawat","year":"2011","journal-title":"J. Org. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/20\/3678\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:25:39Z","timestamp":1760189139000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/20\/3678"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10,12]]},"references-count":23,"journal-issue":{"issue":"20","published-online":{"date-parts":[[2019,10]]}},"alternative-id":["molecules24203678"],"URL":"https:\/\/doi.org\/10.3390\/molecules24203678","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,10,12]]}}}