{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T01:55:44Z","timestamp":1776304544927,"version":"3.50.1"},"reference-count":56,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2022,9,11]],"date-time":"2022-09-11T00:00:00Z","timestamp":1662854400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"NSFC","doi-asserted-by":"publisher","award":["22171215"],"award-info":[{"award-number":["22171215"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"NSFC","doi-asserted-by":"publisher","award":["2022A1515010246"],"award-info":[{"award-number":["2022A1515010246"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"GuangDong Basic and Applied Basic Research Foundation","award":["22171215"],"award-info":[{"award-number":["22171215"]}]},{"name":"GuangDong Basic and Applied Basic Research Foundation","award":["2022A1515010246"],"award-info":[{"award-number":["2022A1515010246"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Carbonyl-containing oxindoles are ubiquitous core structures present in many biologically active natural products and pharmaceutical molecules. Nickel-catalyzed reductive aryl-acylation of alkenes using aryl anhydrides or alkanoyl chlorides as acyl sources is developed, providing 3,3-disubstituted oxindoles bearing ketone functionality at the 3-position. Moreover, nickel-catalyzed reductive aryl-esterification of alkenes using chloroformate as ester sources is further developed, affording 3,3-disubstituted oxindoles bearing ester functionality at the 3-position. This strategy has the advantages of good yields and high functional group compatibility.<\/jats:p>","DOI":"10.3390\/molecules27185899","type":"journal-article","created":{"date-parts":[[2022,9,13]],"date-time":"2022-09-13T01:44:03Z","timestamp":1663033443000},"page":"5899","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes"],"prefix":"10.3390","volume":"27","author":[{"given":"Zhengtian","family":"Ding","sequence":"first","affiliation":[{"name":"The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3260-0097","authenticated-orcid":false,"given":"Wangqing","family":"Kong","sequence":"additional","affiliation":[{"name":"The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/j.pbb.2012.09.023","article-title":"Convolutamydine A and synthetic analogues have antinociceptive properties in mice","volume":"103","author":"Figueirdo","year":"2013","journal-title":"Pharmacol. Biochem. Be."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1933","DOI":"10.1016\/j.fct.2008.01.033","article-title":"Isolation and characterization of new lactam compounds that inhibit lung and colon cancer cells from adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) bran","volume":"46","author":"Lee","year":"2008","journal-title":"Food Chem. Toxicol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1118","DOI":"10.1006\/bbrc.2001.4911","article-title":"AG-041R, a Gastrin\/CCK-B Antagonist, Stimulates Chondrocyte Proliferation and Metabolism in Vitro","volume":"283","author":"Ochi","year":"2001","journal-title":"Biochem. Bioph. Res. Co."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"11258","DOI":"10.1021\/acs.joc.5b02053","article-title":"Access to the Surugatoxin Alkaloids: Chemo-, Regio-, and Stereoselective Oxindole Annulation","volume":"80","author":"Hinze","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1026","DOI":"10.1039\/D0QO01085E","article-title":"Stereoselective synthesis and applications of spirocyclic oxindoles","volume":"8","author":"Boddy","year":"2021","journal-title":"Org. Chem. Front."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2209","DOI":"10.1002\/ejoc.200300050","article-title":"Construction of Spiro[pyrrolidine-3,3\u2032-oxindoles]-Recent Applications to the Synthesis of Oxindole Alkaloids","volume":"12","author":"Marti","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1039\/C1SC00544H","article-title":"Recent progress in enantioselective synthesis of C3-functionalized oxindoles: Rare earth metals take action","volume":"3","author":"Shen","year":"2012","journal-title":"Chem. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7247","DOI":"10.1039\/c2cs35100e","article-title":"Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones","volume":"41","author":"Dalpozzo","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2571","DOI":"10.1016\/j.tetlet.2014.01.084","article-title":"Catalytic asymmetric synthesis of 3,3-disubstituted oxindoles: Diazooxindole joins the field","volume":"55","author":"Cao","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1443","DOI":"10.1021\/acs.accounts.8b00097","article-title":"Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles","volume":"51","author":"Cao","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1562","DOI":"10.1002\/anie.201806088","article-title":"Construction of Quaternary Stereocenters by Palladium Catalyzed Carbopalladation-Initiated Cascade Reactions","volume":"58","author":"Ping","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1021\/acs.accounts.0c00297","article-title":"Metal-Catalyzed Approaches toward the Oxindole Core","volume":"53","author":"Marchese","year":"2020","journal-title":"Acc. Chem. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1021\/ja9093956","article-title":"Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides","volume":"132","author":"Everson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2138","DOI":"10.1021\/ol200617f","article-title":"Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halide","volume":"13","author":"Yu","year":"2011","journal-title":"Org. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1007\/3-540-61454-0_72","article-title":"Organic electroreductive coupling reactions using transition metal complexes as catalysts","volume":"185","author":"Troupel","year":"1997","journal-title":"Top. Curr. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"6828","DOI":"10.1002\/chem.201402302","article-title":"Reductive Cross-Coupling Reactions between Two Electrophiles","volume":"20","author":"Knappke","year":"2014","journal-title":"Chem. \u2013A Eur. J."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"8242","DOI":"10.1002\/chem.201402509","article-title":"Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds","volume":"20","author":"Moragas","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4793","DOI":"10.1021\/jo500507s","article-title":"Cross-Electrophile Coupling: Principles of Reactivity and Selectivity","volume":"79","author":"Everson","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1038\/nature13274","article-title":"Recent advances in homogeneous nickel catalysis","volume":"509","author":"Tasker","year":"2014","journal-title":"Nature"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1039\/C5QO00224A","article-title":"Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: Concept and mechanistic considerations","volume":"2","author":"Gu","year":"2015","journal-title":"Org. Chem. Front."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2344","DOI":"10.1021\/acs.accounts.5b00223","article-title":"Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers and Esters","volume":"48","author":"Tollefson","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1767","DOI":"10.1021\/acs.accounts.5b00057","article-title":"Methods and Mechanisms for Cross-Electrophile Coupling of Csp2 Halides with Alkyl Electrophiles","volume":"48","author":"Weix","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9587","DOI":"10.1021\/acs.chemrev.5b00162","article-title":"Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents to Construct C\u2013C Bonds","volume":"115","author":"Cherney","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1007\/s41061-016-0042-2","article-title":"Nickel-Catalyzed Reductive Couplings","volume":"374","author":"Wang","year":"2016","journal-title":"Top Curr. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1038\/s41570-017-0065","article-title":"Stereospecific and stereoconvergent cross-couplings between alkyl electrophiles","volume":"1","author":"Lucas","year":"2017","journal-title":"Nat. Rev. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1055\/s-0036-1591853","article-title":"Recent Advances in Nickel Catalysis Enabled by Stoichiometric Metallic Reducing Agents","volume":"50","author":"Richmond","year":"2018","journal-title":"Synthesis"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"8542","DOI":"10.1021\/acscatal.0c02115","article-title":"Nickel-Catalyzed Dicarbofunctionalization of Alkenes","volume":"10","author":"Qi","year":"2020","journal-title":"ACS Catal."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8237","DOI":"10.1021\/acscatal.0c01842","article-title":"Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions","volume":"10","author":"Poremba","year":"2020","journal-title":"ACS Catal."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4162","DOI":"10.1039\/D0CS01107J","article-title":"Nickel-catalyzed formation of quaternary carbon centers using tertiary alkyl electrophiles","volume":"50","author":"Xue","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7589","DOI":"10.1021\/acs.joc.2c00462","article-title":"Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations","volume":"87","author":"Charboneau","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6039","DOI":"10.1002\/chem.201200190","article-title":"Nickel-Mediated Inter- and Intramolecular Reductive Cross-Coupling of Unactivated Alkyl bromides and Aryl iodides at Room Temperature","volume":"18","author":"Yan","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2558","DOI":"10.1039\/C8CC00358K","article-title":"Ni-Catalyzed Two-Component Reductive Dicarbofunctionalization of Alkenes via Radical Cyclization","volume":"54","author":"Kuang","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"12364","DOI":"10.1021\/jacs.8b08190","article-title":"Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization\/Cross-Coupling","volume":"140","author":"Wang","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6722","DOI":"10.1002\/anie.201901067","article-title":"Ni-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes","volume":"58","author":"Jin","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"7637","DOI":"10.1021\/jacs.9b03863","article-title":"Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes","volume":"141","author":"Tian","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3305","DOI":"10.1039\/C9QO00744J","article-title":"Ni-Catalyzed Enantioselective Reductive Aryl-Alkenylation of Alkenes: Application to the Synthesis of (+)-Physovenine and (+)-Physostigmine","volume":"6","author":"Li","year":"2019","journal-title":"Org. Chem. Front."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"7335","DOI":"10.1021\/acscatal.9b02081","article-title":"Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines","volume":"9","author":"Ping","year":"2019","journal-title":"ACS Catal."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"9127","DOI":"10.1021\/acscatal.9b03172","article-title":"Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes","volume":"9","author":"Ma","year":"2019","journal-title":"ACS Catal."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2724","DOI":"10.1021\/acs.orglett.0c00688","article-title":"Ni-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes","volume":"22","author":"Jin","year":"2020","journal-title":"Org. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1038\/s42004-020-0292-3","article-title":"Nickel-Catalyzed Enantioselective Reductive Carbo-Acylation of Alkenes","volume":"3","author":"Lan","year":"2020","journal-title":"Commun. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1055\/s-0039-1690807","article-title":"Ni-Catalyzed Reductive Difunctionalization of Alkenes","volume":"52","author":"Ping","year":"2020","journal-title":"Synthesis"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"10204","DOI":"10.1039\/D0SC04173D","article-title":"Stereoselective synthesis of pentasubstituted 1,3-dienes via Ni-catalyzed reductive coupling of unsymmetrical internal alkynes","volume":"11","author":"Zhou","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"6982","DOI":"10.1021\/acs.orglett.0c02534","article-title":"Ni-Catalyzed Reductive Antiarylative Cyclization of Alkynones","volume":"22","author":"Zhou","year":"2020","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"14068","DOI":"10.1002\/anie.202102769","article-title":"Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2","volume":"60","author":"Chen","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"6466","DOI":"10.1021\/acs.orglett.1c02270","article-title":"Ni-Catalyzed Reductive Arylcyanation of Alkenes","volume":"23","author":"Li","year":"2021","journal-title":"Org. Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"10282","DOI":"10.1021\/jacs.1c03827","article-title":"Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes","volume":"143","author":"Pan","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"e202201574","DOI":"10.1002\/anie.202201574","article-title":"Ni-Catalyzed Divergent Synthesis of 2-Benzazepine Derivatives via Tunable Cyclization and 1,4-Acyl Transfer Triggered by Amide N-C Bond Cleavage","volume":"61","author":"Ping","year":"2022","journal-title":"Angew. Chem. Int. Ed"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"11626","DOI":"10.1021\/jacs.2c02487","article-title":"Switchable 1,2-Rearrangement Enables Expedient Synthesis of Structurally Diverse Fluorine-Containing Scaffolds","volume":"144","author":"Ping","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7498","DOI":"10.1021\/acs.orglett.9b02788","article-title":"Ni-Catalyzed Reductive Arylacylation of Alkenes toward Carbonyl-Containing Oxindoles","volume":"21","author":"Xu","year":"2019","journal-title":"Org. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1510","DOI":"10.31635\/ccschem.021.202101040","article-title":"Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes","volume":"4","author":"Jin","year":"2022","journal-title":"CCS Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"3292","DOI":"10.1002\/chem.201504985","article-title":"Visible-Light-Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation\/Semipinacol Rearrangement","volume":"22","author":"Bergonzini","year":"2016","journal-title":"Chem. Eur. J."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1331","DOI":"10.1039\/C7QO00012J","article-title":"Aroyl chlorides as novel acyl radical precursors via visible-light photoredox catalysis","volume":"4","author":"Xu","year":"2017","journal-title":"Org. Chem. Front."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1462","DOI":"10.1039\/C5CC08253F","article-title":"Photocatalyst-free hypervalent iodine reagent catalyzed decarboxylative acylarylation of acrylamides with \u03b1-oxocarboxylic acids driven by visible-light irradiation","volume":"52","author":"Ji","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1034","DOI":"10.1021\/acs.orglett.5b00144","article-title":"UV Light-Mediated Difunctionalization of Alkenes through Aroyl Radical Addition\/1,4-\/1,2-Aryl Shift Cascade Reactions","volume":"17","author":"Zheng","year":"2015","journal-title":"Org. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3466","DOI":"10.1016\/j.tet.2014.03.062","article-title":"Synthesis of oxindole-3-acetates through iron-catalyzed oxidative arylalkoxycarbonylation of activated alkenes","volume":"70","author":"Wang","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2222","DOI":"10.1002\/adsc.201300468","article-title":"Silver-Catalyzed Decarboxylative Acylarylation of Acrylamides with \u03b1-Oxocarboxylic Acids in Aqueous Media","volume":"355","author":"Wang","year":"2013","journal-title":"Adv. Synth. Catal."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/18\/5899\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:29:28Z","timestamp":1760142568000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/18\/5899"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,11]]},"references-count":56,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["molecules27185899"],"URL":"https:\/\/doi.org\/10.3390\/molecules27185899","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,11]]}}}