{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:18:41Z","timestamp":1760149121922,"version":"build-2065373602"},"reference-count":81,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,7,5]],"date-time":"2023-07-05T00:00:00Z","timestamp":1688515200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT), Portugal","award":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"]}]},{"name":"RUDN University Strategic Academic Leadership Program","award":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020","UIDP\/00100\/2020","LA\/P\/0056\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Catalysts"],"abstract":"<jats:p>Nitrogen-containing heterocycles such as morpholin-2-ones are structural elements of many biologically active substances, as well as useful synthetic intermediates. To be able to functionalize them regioselectively in an easy, atom-efficient, and environmentally friendly manner is highly desirable. A procedure for cross-dehydrogenative coupling between morpholinones and cyclic imides was developed addressing these requirements. An earth-abundant metal catalyst, copper(I) chloride, in the presence of acetic acid, and with molecular oxygen as the sole oxidant, operating under mild conditions, afforded the desired C\u2013N coupled products in high yields. Besides being potentially biologically active, as many members of both families of compounds are, the products themselves may be suitable substrates for functionalized polymers, e.g., poly(\u03b2-aminoesters) or even for PROTACs.<\/jats:p>","DOI":"10.3390\/catal13071072","type":"journal-article","created":{"date-parts":[[2023,7,6]],"date-time":"2023-07-06T00:34:30Z","timestamp":1688603670000},"page":"1072","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["A Mild and Sustainable Procedure for the Functionalization of Morpholin-2-Ones by Oxidative Imidation Reactions"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3101-016X","authenticated-orcid":false,"given":"Ana Maria","family":"Faisca Phillips","sequence":"first","affiliation":[{"name":"Coordination Chemistry and Catalysis Group, Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando J. L.","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Coordination Chemistry and Catalysis Group, Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal"},{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia (RUDN University), 117198 Moscow, Russia"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6789","DOI":"10.1039\/D1GC01871J","article-title":"Cross-dehydrogenative coupling: A sustainable reaction for C\u2013C bond formations","volume":"23","author":"Tian","year":"2021","journal-title":"Green Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Faisca Phillips, A.M., Guedes da Silva, M.d.F.C., and Pombeiro, A.J.L. (2020). New trends in enantioselective cross-dehydrogenative coupling. Catalysts, 10.","DOI":"10.3390\/catal10050529"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"12705","DOI":"10.1021\/acs.joc.9b01704","article-title":"En route to intermolecular cross-dehydrogenative coupling Reactions","volume":"84","author":"Huang","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"9683","DOI":"10.1039\/C9OB02113B","article-title":"Catalytic enantioselective cross dehydrogenative coupling of sp3 C\u2013H of heterocycles","volume":"17","author":"Gandhi","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3354","DOI":"10.1002\/cctc.201800582","article-title":"Recent developments in transition metal-catalyzed cross-dehydrogenative coupling reactions of ethers and thioethers","volume":"10","author":"Phillips","year":"2018","journal-title":"ChemCatChem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1016\/j.tetlet.2017.01.035","article-title":"Recent advancements in dehydrogenative cross coupling reactions for C\u2013C bond formation","volume":"58","author":"Varun","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1021\/acs.accounts.6b00637","article-title":"Oxidative coupling in complexity building transforms","volume":"50","author":"Kozlowski","year":"2017","journal-title":"Acc. Chem. Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12138","DOI":"10.1021\/cr500431s","article-title":"Oxidative coupling between two hydrocarbons: An update of recent C-H functionalizations","volume":"115","author":"Liu","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1021\/cr100280d","article-title":"Catalytic dehydrogenative cross-coupling: Forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds","volume":"111","author":"Yeung","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Maiti, D. (2022). Handbook of CH-Functionalization, Wiley-VCH.","DOI":"10.1002\/9783527834242"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2853","DOI":"10.1055\/s-0037-1610073","article-title":"Cross-dehydrogenative coupling reactions for the functionalization of \u03b1-amino acid derivatives and peptides","volume":"50","author":"Correa","year":"2018","journal-title":"Synthesis"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"8775","DOI":"10.1021\/cr500200x","article-title":"C\u2013H functionalization in the synthesis of amino acids and peptides","volume":"114","author":"Noisier","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"5288","DOI":"10.1021\/acs.orglett.7b02567","article-title":"Co-catalyzed C(sp3)\u2013H oxidative coupling of glycine and peptide derivatives","volume":"19","author":"Guerrero","year":"2017","journal-title":"Org. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2174","DOI":"10.1021\/cr500399p","article-title":"Advances in chemical protein modification","volume":"115","author":"Boutureira","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1691","DOI":"10.1039\/C4CS00388H","article-title":"Towards the next generation of biomedicines by site-selective conjugation","volume":"45","author":"Hu","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/j.drudis.2016.11.003","article-title":"Peptidomimetic therapeutics: Scientific approaches and opportunities","volume":"22","author":"Qvit","year":"2017","journal-title":"Drug Discov. Today"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"10807","DOI":"10.1021\/acs.jmedchem.6b00319","article-title":"Unusual amino acids in medicinal chemistry","volume":"59","author":"Blaskovich","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1007\/s00253-003-1274-y","article-title":"Industrial production of \u03b2-lactam antibiotics","volume":"61","author":"Elander","year":"2003","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3661","DOI":"10.1002\/chem.201903917","article-title":"Racemisation in Chemistry and Biology","volume":"26","author":"Ballard","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4312","DOI":"10.1002\/anie.201206835","article-title":"Recent developments in asymmetric phase-transfer reactions","volume":"52","author":"Shirakawa","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5656","DOI":"10.1021\/cr068368n","article-title":"Recent development and application of chiral phase-transfer catalysts","volume":"107","author":"Hashimoto","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Barrett, G.C. (1985). Chemistry and Biochemistry of the Amino Acids, Springer.","DOI":"10.1007\/978-94-009-4832-7"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1039\/D0CS00344A","article-title":"Photocatalytic methods for amino acid modification","volume":"50","author":"King","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6176","DOI":"10.1002\/anie.201807536","article-title":"Metal-Mediated Functionalization of Natural peptides and proteins: Panning for bioconjugation gold","volume":"58","author":"Ohata","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3863","DOI":"10.1021\/acs.biochem.7b00536","article-title":"Residue-specific peptide modification: A chemist\u2019s guide","volume":"56","author":"Malins","year":"2017","journal-title":"Biochemistry"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1966","DOI":"10.1021\/acs.oprd.1c00208","article-title":"Synthesis of enantiopure unnatural amino acids by metallaphotoredox catalysis","volume":"25","author":"Faraggi","year":"2021","journal-title":"Org. Process Res. Dev."},{"key":"ref_27","unstructured":"Mani, V.S., and Narayanasamy, R. (2016). Conformationally constrained amino acids in peptide design. SSRN."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"566","DOI":"10.2174\/1568026618666180522075258","article-title":"Designing peptidomimetics","volume":"18","author":"Perez","year":"2018","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3262","DOI":"10.1039\/D0CS00102C","article-title":"Peptidomimetic toolbox for drug discovery","volume":"49","author":"Lenci","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Robertson, N.S., and Spring, D.R. (2018). Using peptidomimetics and constrained peptides as valuable tools for inhibiting protein\u2013protein interactions. Molecules, 23.","DOI":"10.3390\/molecules23040959"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1038\/nrd.2018.125","article-title":"Constrained peptides\u2019 time to shine?","volume":"17","author":"Morrison","year":"2018","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5387","DOI":"10.1039\/D2OB00678B","article-title":"Eosin-Y\/Cu(OAc)2-catalyzed aerobic oxidative coupling reactions of glycine esters in the dark","volume":"20","author":"Chowdhury","year":"2022","journal-title":"Org. Biomol. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1039\/C7QO00851A","article-title":"Cu(i)-Catalyzed amidation\/imidation of N-arylglycine ester derivatives via C\u2013N coupling under mild conditions","volume":"5","author":"Daggupati","year":"2018","journal-title":"Org. Chem. Front."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2902","DOI":"10.1039\/C8OB00176F","article-title":"A copper\/O2-mediated direct sp3 C\u2013H\/N\u2013H cross-dehydrogen coupling reaction of acylated amines and N-aryl glycine esters","volume":"16","author":"Sun","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1659","DOI":"10.1055\/s-0036-1591586","article-title":"Copper-catalyzed cross-dehydrogenative-coupling reaction of N-arylglycine esters with imides or amides for synthesis of \u03b1-substituted \u03b1-amino acid esters","volume":"29","author":"Xiao","year":"2018","journal-title":"Synlett"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"13341","DOI":"10.1039\/C6CC05885J","article-title":"Iron-catalyzed oxidative sp3 carbon-hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones","volume":"52","author":"Huo","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1515\/hc-2022-0007","article-title":"Ionic liquid-catalyzed synthesis of (1,4-benzoxazin-3-yl) malonate derivatives via cross-dehydrogenative-coupling reactions","volume":"28","author":"Sharifi","year":"2022","journal-title":"Heterocycl. Commun."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1016\/S0957-4166(97)00058-X","article-title":"Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine","volume":"8","author":"Ashwood","year":"1997","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3551","DOI":"10.1055\/s-0032-1316797","article-title":"Advances in the synthesis of morpholin-3-ones and morpholin-2-ones","volume":"44","author":"Trstenjak","year":"2012","journal-title":"Synthesis"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1016\/S1874-6004(05)80033-4","article-title":"Synthesis of aprepitant","volume":"Volume 6","author":"Harmata","year":"2005","journal-title":"Strategies and Tactics in Organic Synthesis"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"5244","DOI":"10.1016\/j.bmcl.2006.05.031","article-title":"Morpholin-2-one derivatives as novel selective T-type Ca2+ channel blockers","volume":"16","author":"Ku","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2472","DOI":"10.1021\/jm401767k","article-title":"Selective and potent morpholinone inhibitors of the MDM2-p53 protein-protein interaction","volume":"57","author":"Gonzalez","year":"2014","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"4854","DOI":"10.1016\/j.bmcl.2012.05.038","article-title":"Haloenol pyranones and morpholinones as antineoplastic agents of prostate cancer","volume":"22","author":"Mock","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1502","DOI":"10.1021\/jm501814x","article-title":"2-(2-oxo-morpholin-3-yl)-acetamide derivatives as broad-spectrum antifungal agents","volume":"58","author":"Bardiot","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"9252","DOI":"10.1021\/ja503830c","article-title":"Organocatalytic ring-opening polymerization of morpholinones: New strategies to functionalized polyesters","volume":"136","author":"Blake","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1021\/jo00265a015","article-title":"Nucleophilic ring-opening reactions of morpholin-2-ones. A resolution of dl-(secondary-alkyl)amines","volume":"54","author":"Kashima","year":"1989","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.addr.2016.08.003","article-title":"Poly(\u03b1-hydroxy acid)s and poly(\u03b1-hydroxy acid-co-\u03b1-amino acid)s derived from amino acid","volume":"107","author":"Basu","year":"2016","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.jconrel.2019.08.024","article-title":"Poly(\u03b2-amino ester)-based gene delivery systems: From discovery to therapeutic applications","volume":"310","author":"Cordeiro","year":"2019","journal-title":"J. Control. Release"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"110097","DOI":"10.1016\/j.eurpolymj.2020.110097","article-title":"Poly(\u03b2-amino esters) based potential drug delivery and targeting polymer; an overview and perspectives (review)","volume":"141","author":"Iqbal","year":"2020","journal-title":"Eur. Polym. J."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"5340","DOI":"10.1002\/cssc.202102243","article-title":"Recent advances in copper-catalyzed C\u2013N bond formation involving N-centered radicals","volume":"14","author":"Zheng","year":"2021","journal-title":"ChemSusChem"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"9247","DOI":"10.1021\/acs.chemrev.6b00644","article-title":"Transition metal-catalyzed C\u2013H amination: Scope, mechanism, and applications","volume":"117","author":"Park","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"9283","DOI":"10.1039\/c3cs60228a","article-title":"C\u2013N bond forming cross-coupling reactions: An overview","volume":"42","author":"Bariwal","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_53","unstructured":"Luzzio, F.A. (2019). Imides: Medicinal, Agricultural, Synthetic Applications and Natural Products Chemistry, Elsevier."},{"key":"ref_54","unstructured":"Li, J.J. (2019). Imides: Medicinal, Agricultural, Synthetic Applications and Natural Products Chemistry, Elsevier."},{"key":"ref_55","unstructured":"Luzzio, F.A. (2019). Imides: Medicinal, Agricultural, Synthetic Applications and Natural Products Chemistry, Elsevier."},{"key":"ref_56","first-page":"495","article-title":"Apremilast (Otezla): A new oral treatment for adults with psoriasis and psoriatic arthritis","volume":"40","author":"Zerilli","year":"2015","journal-title":"Pharm. Ther."},{"key":"ref_57","unstructured":"(2010). In Top 200 Pharmaceuticals by Retail Sales in 2021, compiled and produced by M. H. Qureshi from the Njar\u00f0arson group (University of Arizona) as described by McGrath, N.A.; Brichacek, M.; Njardarson, J.T. A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives. J. Chem. Ed., 87, 1348\u20131349. Available online: https:\/\/njardarson.lab.arizona.edu\/sites\/njardarson.lab.arizona.edu\/files\/Top%20200%20Pharmaceuticals%202021V2.pdf."},{"key":"ref_58","unstructured":"(2010). In Top 200 Small Molecule Pharmaceuticals by Retail Sales in 2021, compiled and produced by M. H. Qureshi from the Njar\u00f0arson group (University of Arizona) as described by McGrath, N.A.; Brichacek, M.; Njardarson, J.T. A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives. J. Chem. Ed., 87, 1348\u20131349. Available online: https:\/\/njardarson.lab.arizona.edu\/sites\/njardarson.lab.arizona.edu\/files\/Top%20200%20Small%20Molecules%202021V3.pdf."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1038\/d41573-021-00052-4","article-title":"Targeted protein degraders crowd into the clinic","volume":"20","author":"Mullard","year":"2021","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1038\/s41573-021-00371-6","article-title":"PROTAC targeted protein degraders: The past is prologue","volume":"21","author":"Langley","year":"2022","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5214","DOI":"10.1039\/D2CS00193D","article-title":"PROTACs: Past, present and future","volume":"51","author":"Li","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"514","DOI":"10.1038\/nchembio.2329","article-title":"Structural basis of PROTAC cooperative recognition for selective protein degradation","volume":"13","author":"Gadd","year":"2017","journal-title":"Nat. Chem. Biol."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1021\/acschembio.7b00969","article-title":"Translation termination factor GSPT1 is a phenotypically relevant off-target of heterobifunctional phthalimide degraders","volume":"13","author":"Ishoey","year":"2018","journal-title":"ACS Chem. Biol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1376","DOI":"10.1126\/science.aab1433","article-title":"Phthalimide conjugation as a strategy for in vivo target protein degradation","volume":"348","author":"Winter","year":"2015","journal-title":"Science"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5250","DOI":"10.1021\/jo1009883","article-title":"Nucleophilic reactivities of imide and amide anions","volume":"75","author":"Breugst","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"6050","DOI":"10.1021\/jo4007199","article-title":"Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: Synthesis of dihydroquinazolines and quinolines","volume":"78","author":"Rohlmann","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1337","DOI":"10.1177\/00220345890680091001","article-title":"Substitutes for N-phenylglycine in adhesive bonding to dentin","volume":"68","author":"Johnston","year":"1989","journal-title":"J. Dent. Res."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"15289","DOI":"10.1021\/acsomega.9b02430","article-title":"Synthetic strategy for pyrazolo[1,5-a]pyridine and pyrido[1,2-b]indazole derivatives through AcOH and O2-promoted cross-dehydrogenative coupling reactions between 1,3-dicarbonyl compounds and N-amino-2-iminopyridines","volume":"4","author":"Behbehani","year":"2019","journal-title":"ACS Omega"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2459","DOI":"10.1021\/acs.orglett.8b00800","article-title":"Stereoselective synthesis of optically pure 2-amino-2\u2032-hydroxy-1,1\u2032-binaphthyls","volume":"20","author":"Forkosh","year":"2018","journal-title":"Org. Lett."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4194","DOI":"10.1021\/ol5018883","article-title":"Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at \u03b1-position of tertiary amines","volume":"16","author":"Ueda","year":"2014","journal-title":"Org. Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"3754","DOI":"10.1021\/ol201439t","article-title":"A metal-free amination of benzoxazoles\u2013The first example of an iodide-catalyzed oxidative amination of heteroarenes","volume":"13","author":"Froehr","year":"2011","journal-title":"Org. Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"11498","DOI":"10.1039\/c3ra41179f","article-title":"Highly enantioselective aza-Michael addition reactions of 4-nitrophthalimide with \u03b1,\u03b2-unsaturated ketones","volume":"3","author":"Ma","year":"2013","journal-title":"RSC Adv."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"2917","DOI":"10.1021\/acs.orglett.7b01152","article-title":"Iron phosphate catalyzed asymmetric cross-dehydrogenative coupling of 2-naphthols with \u03b2-ketoesters","volume":"19","author":"Narute","year":"2017","journal-title":"Org. Lett."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"6212","DOI":"10.1021\/jacs.8b03063","article-title":"An enantioselective cross-dehydrogenative coupling catalysis approach to substituted tetrahydropyrans","volume":"140","author":"Lee","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_75","unstructured":"World Health Organization (2019). World Health Organization Model List of Essential Medicines: 22nd List 2019."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1021\/acscatal.7b02974","article-title":"Oxidative coupling mechanisms: Current state of understanding","volume":"8","author":"Maseras","year":"2018","journal-title":"ACS Catal."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"6234","DOI":"10.1021\/cr300527g","article-title":"Aerobic copper-catalyzed organic reactions","volume":"113","author":"Allen","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"11062","DOI":"10.1002\/anie.201103945","article-title":"Copper-catalyzed aerobic oxidative C\u2013H functionalizations: Trends and mechanistic insights","volume":"50","author":"Wendlandt","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1002\/cplu.201300117","article-title":"Computational studies on the mechanism of the copper-catalyzed sp3-C\u2013H cross-dehydrogenative coupling reaction","volume":"78","author":"Cheng","year":"2013","journal-title":"ChemPlusChem"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"2155","DOI":"10.1021\/jo00294a032","article-title":"Synthesis and characterization of di-disubstituted phthalocyanines","volume":"55","author":"Young","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/s10973-011-1601-y","article-title":"Thermal characteristics of precursors to a difunctional imide monomer","volume":"106","author":"Howell","year":"2011","journal-title":"J. Therm. Anal. Calorim."}],"container-title":["Catalysts"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4344\/13\/7\/1072\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:06:25Z","timestamp":1760126785000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4344\/13\/7\/1072"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,5]]},"references-count":81,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2023,7]]}},"alternative-id":["catal13071072"],"URL":"https:\/\/doi.org\/10.3390\/catal13071072","relation":{},"ISSN":["2073-4344"],"issn-type":[{"type":"electronic","value":"2073-4344"}],"subject":[],"published":{"date-parts":[[2023,7,5]]}}}