{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T21:05:56Z","timestamp":1792789556576,"version":"4.5.0"},"reference-count":50,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2022,7,29]],"date-time":"2022-07-29T00:00:00Z","timestamp":1659052800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Hubei Provincial Natural Science Foundation of China","award":["2019CFB363"],"award-info":[{"award-number":["2019CFB363"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The use of simple, inexpensive, and efficient methods to construct carbon\u2013boron and carbon\u2013oxygen bonds has been a hot research topic in organic synthesis. We demonstrated that the desired \u03b2-boronic acid products can be obtained under mild conditions using copper foam as an efficient heterogeneous catalyst. The structure of copper foam before and after the reaction was investigated by polarized light microscopy (PM), scanning electron microscopy (SEM), and transmission electron microscopy (TEM), and the results have shown that the structure of the catalyst copper foam remained unchanged before and after the reaction. The XPS test results showed that the Cu(0) content increased after the reaction, indicating that copper may be involved in the boron addition reaction. The specific optimization conditions were as follows: CH3COCH3 and H2O were used as mixed solvents, 4-methoxychalcone was used as the raw material, 8 mg of catalyst was used and the reaction was carried out at room temperature and under air for 10 h. The yield of the product obtained was up to 92%, and the catalytic efficiency of the catalytic material remained largely unchanged after five cycles of use.<\/jats:p>","DOI":"10.3390\/ijms23158403","type":"journal-article","created":{"date-parts":[[2022,7,31]],"date-time":"2022-07-31T23:37:29Z","timestamp":1659310649000},"page":"8403","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Copper Foam as Active Catalysts for the Borylation of \u03b1, \u03b2-Unsaturated Compounds"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0970-4840","authenticated-orcid":false,"given":"Kewang","family":"Zheng","sequence":"first","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"},{"name":"Hubei Key Laboratory of Biological Resources and Environmental Biotechnology, Wuhan University, Wuhan 430079, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miao","family":"Liu","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhifei","family":"Meng","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zufeng","family":"Xiao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fei","family":"Zhong","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9772-3034","authenticated-orcid":false,"given":"Caiqin","family":"Qin","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,7,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2909","DOI":"10.1021\/jm900125m","article-title":"Design, synthesis, and biological activity of boronic acid-based histone deacetylase inhibitors","volume":"52","author":"Suzuki","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1002\/aoc.2880","article-title":"Biological activity of selected boronic acids and their derivatives","volume":"26","author":"Misterkiewicz","year":"2012","journal-title":"Appl. Organomet. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"12232","DOI":"10.1021\/acsami.8b21862","article-title":"Strongly enhanced antibacterial action of copper oxide nanoparticles with boronic acid surface functionality","volume":"11","author":"Halbus","year":"2019","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1007\/3-540-45313-X_2","article-title":"Organoboron compounds","volume":"29","author":"Miyaura","year":"2002","journal-title":"Cross-Coupling React."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1002\/tcr.10068","article-title":"Metal-catalyzed reactions of diborons for synthesis of organoboron compounds","volume":"3","author":"Ishiyama","year":"2004","journal-title":"Chem. Rec."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Tevyashova, A.N., and Chudinov, M.V. (2021). Progress in the medical chemistry of organoboron compounds. Russ. Chem. Rev., 90.","DOI":"10.1070\/RCR4977"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Manna, S., Das, K.K., Nandy, S., Aich, D., Paul, S., and Panda, S. (2021). A new avenue for the preparation of organoboron compounds via nickel catalysis. Coord. Chem. Rev., 448.","DOI":"10.1016\/j.ccr.2021.214165"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"890","DOI":"10.1021\/cr900206p","article-title":"C\u2212H activation for the construction of C\u2212B bonds","volume":"110","author":"Mkhalid","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1603","DOI":"10.1021\/jacs.9b12519","article-title":"Visible light-induced borylation of C\u2013O, C\u2013N, and C\u2013X bonds","volume":"142","author":"Jin","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Lee, K.-S., Zhugralin, A., and Hoveyda, A. (2009). NHC-Catalyzed Boron Conjugate Additions to \u03b1,\u03b2-Unsaturated Carbonyl Compounds. Synfacts, 2009.","DOI":"10.1055\/s-0029-1217488"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Gao, M., Thorpe, S., Kleeberg, C., Slebodnick, C., Marder, T., and Santos, W. (2011). Catalytic Regioselective Boration of \u03b1, \u03b2-Unsaturated Compounds. Synfacts, 2011.","DOI":"10.1055\/s-0030-1260878"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1559","DOI":"10.1002\/adsc.202001407","article-title":"Recent Trends and Prospects in the Copper-Catalysed \u201con Water\u201d Reactions","volume":"363","author":"Shilpa","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1641","DOI":"10.1021\/jacs.0c12453","article-title":"Palladium-catalyzed synthesis of dibenzosilepin derivatives via 1, n-Palladium migration coupled with anti-Carbopalladation of alkyne","volume":"143","author":"Tsuda","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"878","DOI":"10.1002\/anie.198508781","article-title":"Catalytic hydroboration with rhodium complexes","volume":"24","year":"1985","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5178","DOI":"10.1021\/jo00256a059","article-title":"Enantioselective hydroboration mediated by homochiral rhodium catalysts","volume":"53","author":"Burgess","year":"1988","journal-title":"J. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"6139","DOI":"10.1021\/ja00016a033","article-title":"Further evidence for the role of d. pi.-p. pi. bonding in rhodium-mediated hydroborations","volume":"113","author":"Burgess","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1016\/S0957-4166(00)86113-3","article-title":"Enantioselective hydroborations catalyzed by rhodium (+1) complexes","volume":"2","author":"Burgess","year":"1991","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2380","DOI":"10.1002\/anie.200462961","article-title":"Palladium-Catalyzed Addition of Cyanoboranes to Alkynes: Regio-and Stereoselective Synthesis of \u03b1,\u03b2-Unsaturated \u03b2-Boryl Nitriles","volume":"44","author":"Suginome","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4443","DOI":"10.1021\/om8006294","article-title":"DFT studies on the borylation of \u03b1,\u03b2-unsaturated carbonyl compounds catalyzed by phosphine copper (I) boryl complexes and observations on the interconversions between O-and C-bound enolates of Cu, B, and Si","volume":"27","author":"Dang","year":"2008","journal-title":"Organometallics"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2520","DOI":"10.1039\/b900741e","article-title":"Axially chiral PN ligands for the copper catalyzed \u03b2-borylation of \u03b1,\u03b2-unsaturated esters","volume":"7","author":"Fleming","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1039\/C0CC02270E","article-title":"Regio-and stereoselective copper-catalyzed \u03b2-borylation of allenoates by a preactivated diboron","volume":"47","author":"Thorpe","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1918","DOI":"10.1021\/ol300575d","article-title":"Unexpected copper (II) catalysis: Catalytic amine base promoted \u03b2-borylation of \u03b1,\u03b2-unsaturated carbonyl compounds in water","volume":"14","author":"Thorpe","year":"2012","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2408","DOI":"10.1002\/adsc.202001616","article-title":"Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and \u03b1,\u03b2-Borylation of \u03b1,\u03b2-Unsaturated Carbonyl Compounds with Bis (Pinacolato) Diboron","volume":"363","author":"Shegavi","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1021\/ja3104389","article-title":"Rh (III)-Catalyzed regioselective synthesis of pyridines from alkenes and \u03b1,\u03b2-unsaturated oxime esters","volume":"135","author":"Neely","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1016\/j.tetasy.2016.05.004","article-title":"Rh-catalyzed asymmetric 1,4-addition reactions to \u03b1,\u03b2-unsaturated carbonyl and related compounds: An update","volume":"27","author":"Heravi","year":"2016","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_26","unstructured":"Romano, C. (2018). Transition Metal-Catalyzed Olefin Isomerization for Remote Functionalization Strategies. [Ph.D. Thesis, University of Geneva]."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1016\/S0065-3055(03)51005-X","article-title":"Recent chemistry of the diboron compounds","volume":"51","author":"Dembitsky","year":"2004","journal-title":"Adv. Organomet. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2051","DOI":"10.1039\/a705743a","article-title":"Platinum catalysed 1, 4-diboration of \u03b1,\u03b2-unsaturated ketones","volume":"21","author":"Lawson","year":"1997","journal-title":"Chem. Commun."},{"key":"ref_29","unstructured":"Cox, A.J. (2002). Metal Catalysed Diboration of \u03b1,\u03b2-Unsaturated Carbonyl Compounds. [Master\u2019s Thesis, Durham University]."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1246\/bcsj.20140158","article-title":"Ni-Catalyzed C\u2013C Bond Formation with \u03b1,\u03b2-Unsaturated Carbonyl Compounds and Alkynes","volume":"87","author":"Kurahashi","year":"2014","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5082","DOI":"10.1039\/C7DT00649G","article-title":"Kinetic investigation into the chemoselective hydrogenation of \u03b1,\u03b2-unsaturated carbonyl compounds catalyzed by Ni (0) nanoparticles","volume":"46","author":"Zaramello","year":"2017","journal-title":"Dalton Trans."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"14291","DOI":"10.1021\/acs.joc.9b02096","article-title":"Chiral Bicyclic NHC\/Cu Complexes for Catalytic Asymmetric Borylation of \u03b1,\u03b2-Unsaturated Esters","volume":"84","author":"Miwa","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"868","DOI":"10.1039\/D0QO00024H","article-title":"Cu2O-catalyzed selective 1,2-addition of acetonitrile to \u03b1,\u03b2-unsaturated aldehydes","volume":"7","author":"Che","year":"2020","journal-title":"Org. Chem. Front."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6821","DOI":"10.1016\/S0040-4039(00)01161-8","article-title":"Boration of an \u03b1,\u03b2-enone using a diboron promoted by a copper (I)\u2013phosphine mixture catalyst","volume":"41","author":"Ito","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1002\/ange.200703699","article-title":"Catalytic Asymmetric Boration of Acyclic \u03b1,\u03b2-Unsaturated Esters and Nitriles","volume":"120","author":"Lee","year":"2008","journal-title":"Angew. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1039\/C5QO00289C","article-title":"Chemoselective catalytic reduction of conjugated \u03b1,\u03b2-unsaturated ketones to saturated ketones via a hydroboration\/protodeboronation strategy","volume":"3","author":"Ding","year":"2016","journal-title":"Org. Chem. Front."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"12763","DOI":"10.1002\/anie.201207343","article-title":"Chiral Copper (II)-Catalyzed Enantioselective Boron Conjugate Additions to \u03b1,\u03b2-Unsaturated Carbonyl Compounds in Water","volume":"51","author":"Kobayashi","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1002\/aoc.2957","article-title":"Basic CuCO3\/ligand as a new catalyst for \u2018on water\u2019 borylation of Michael acceptors, alkenes and alkynes: Application to the efficient asymmetric synthesis of \u03b2-alcohol type sitagliptin side chain","volume":"27","author":"Stavber","year":"2013","journal-title":"Appl. Organomet. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Deng, F., Li, S., Zhou, M., Zhu, Y., Qiu, S., Li, K., Ma, F., and Jiang, J. (2019). A biochar modified nickel-foam cathode with iron-foam catalyst in electro-Fenton for sulfamerazine degradation. Appl. Catal. B Environ., 256.","DOI":"10.1016\/j.apcatb.2019.117796"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.apenergy.2019.03.199","article-title":"Novel copper foam with ordered hole arrays as catalyst support for methanol steam reforming microreactor","volume":"246","author":"Liu","year":"2019","journal-title":"Appl. Energy"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1016\/j.scitotenv.2018.08.003","article-title":"Application of nickel foam-supported Co3O4-Bi2O3 as a heterogeneous catalyst for BPA removal by peroxymonosulfate activation","volume":"647","author":"Hu","year":"2019","journal-title":"Sci. Total Environ."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6734","DOI":"10.1016\/j.ijhydene.2020.11.111","article-title":"A thermally autonomous methanol steam reforming microreactor with porous copper foam as catalyst support for hydrogen production","volume":"46","author":"Wang","year":"2021","journal-title":"Int. J. Hydrogen Energy"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2074","DOI":"10.6023\/cjoc202011017","article-title":"Zeolite Immobilized Copper Catalyzed Conjugate Borylation of alpha, beta-Unsaturated Compounds in Aqueous Media","volume":"41","author":"Yan","year":"2021","journal-title":"Chin. J. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Wang, W., Xiao, Z., Huang, C., Zheng, K., Luo, Y., Dong, Y., Shen, Z., Li, W., and Qin, C. (2019). Preparation of Modified Chitosan Microsphere-Supported Copper Catalysts for the Borylation of \u03b1,\u03b2-Unsaturated Compounds. Polymers, 11.","DOI":"10.3390\/polym11091417"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Wen, W., Han, B., Yan, F., Ding, L., Li, B., Wang, L., and Zhu, L. (2018). Borylation of \u03b1,\u03b2-Unsaturated Acceptors by Chitosan Composite Film Supported Copper Nanoparticles. Nanomaterials, 8.","DOI":"10.3390\/nano8050326"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3220","DOI":"10.1007\/s10562-021-03571-2","article-title":"Cellulosic CuI Nanoparticles as a Heterogeneous, Recyclable Catalyst for the Borylation of \u03b1,\u03b2-Unsaturated Acceptors in Aqueous Media","volume":"151","author":"Zhou","year":"2021","journal-title":"Catal. Lett."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1016\/j.gee.2020.09.002","article-title":"Hierarchical Cu3P-based nanoarrays on nickel foam as efficient electrocatalysts for overall water splitting","volume":"7","author":"Yang","year":"2020","journal-title":"Green Energy Environ."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.catcom.2016.08.002","article-title":"A green and recyclable chitosan supported catalyst for the borylation of \u03b1,\u03b2-unsaturated acceptors in water","volume":"86","author":"Xu","year":"2016","journal-title":"Catal. Commun."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"11685","DOI":"10.1039\/C5CC04295J","article-title":"A Cu (II)-based strategy for catalytic enantioselective \u03b2-borylation of \u03b1,\u03b2-unsaturated acceptors","volume":"51","author":"Zhu","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"5691","DOI":"10.1016\/j.tet.2016.07.079","article-title":"Borylation and selective reduction of \u03b1,\u03b2-unsaturated ketones under mild conditions catalyzed by Cu nanoparticles","volume":"72","author":"Zhou","year":"2016","journal-title":"Tetrahedron"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/15\/8403\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:59:09Z","timestamp":1760140749000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/15\/8403"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,29]]},"references-count":50,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2022,8]]}},"alternative-id":["ijms23158403"],"URL":"https:\/\/doi.org\/10.3390\/ijms23158403","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,7,29]]}}}