{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T14:06:27Z","timestamp":1789135587057,"version":"build-2803163510"},"reference-count":31,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T00:00:00Z","timestamp":1787702400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T00:00:00Z","timestamp":1787702400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T00:00:00Z","timestamp":1787702400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100012515","name":"Cyrus Tang Foundation","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100012515","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21971174"],"award-info":[{"award-number":["21971174"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["U2267224"],"award-info":[{"award-number":["U2267224"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007824","name":"Soochow University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100007824","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012246","name":"Priority Academic Program Development of Jiangsu Higher Education Institutions","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100012246","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Jiangsu Qing-Lan Project for Young and Middle-aged Academic Leaders","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Herein, we report the development of a three-component radical cascade for the synthesis of sulfonylated oxindoles from a sulfonamide derivative, bis(1,4-diazabicyclo[2.2.2]octane) sulfur dioxide (DABSO), and benzenediazonium tetraarylborate salts. Remarkably, the transformation operates under both photocatalytic and nonphotocatalytic conditions, providing flexible access to the desired products. The reaction proceeds through in situ generation of a sulfonyl radical, followed by addition to the alkene, a Truce\u2013Smiles-type 1,4-cyano migration, and subsequent intramolecular cyclization to construct the oxindole framework. This one-pot cascade enables the formation of C\u2013S and C\u2013C bonds under mild conditions. The method delivers a broad range of sulfonylated oxindoles in generally good yields with wide functional group tolerance and high atom economy, and in situ capture of substrate-released SO2 by the diazonium salt enabled the use of only 0.5 equiv of DABSO as the SO2 surrogate, offering a concise and efficient route to highly substituted oxindole derivatives.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01612","type":"journal-article","created":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T13:40:27Z","timestamp":1788270027000},"page":"12401-12412","source":"Crossref","is-referenced-by-count":0,"title":["Radical-Mediated Functional\nGroup Migration and Cyclization\nCascade for the Synthesis of Sulfonylated Oxindoles"],"prefix":"10.1021","volume":"91","author":[{"given":"Syed Anis Ali","family":"Shah","sequence":"first","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daopeng","family":"Sheng","sequence":"additional","affiliation":[{"name":"Soochow University , , , ,","place":["Suzhou, Jiangsu, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo-Xi","family":"Liu","sequence":"additional","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi-Xin","family":"Xing","sequence":"additional","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hai","family":"Li","sequence":"additional","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu-xiao","family":"Ding","sequence":"additional","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6088-7278","authenticated-orcid":true,"given":"Weidong","family":"Rao","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shu-Su","family":"Shen","sequence":"additional","affiliation":[{"name":"Suzhou University of Science and Technology , , ,","place":["Suzhou, P. R. China, 215009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8985-8753","authenticated-orcid":true,"given":"Shun-Yi","family":"Wang","sequence":"additional","affiliation":[{"name":"Soochow University , , ,","place":["Suzhou, China, 215123"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,26]]},"reference":[{"issue":"6","key":"2026091109105460100_cit1a","doi-asserted-by":"publisher","first-page":"793","DOI":"10.1002\/med.20074","article-title":"Vinyl sulfones: Synthetic preparations\nand medicinal chemistry applications","volume":"26","author":"Meadows","year":"2006","journal-title":"Med. Res.\nRev"},{"issue":"61","key":"2026091109105460100_cit1b","doi-asserted-by":"publisher","first-page":"8995","DOI":"10.1039\/C9CC03789F","article-title":"Transition-metal-\nand oxidant-free directed anodic C\u2013H sulfonylation of N,N-disubstituted\nanilines with sulfinates","volume":"55","author":"Wu","year":"2019","journal-title":"Chem.Commun"},{"issue":"6","key":"2026091109105460100_cit1c","doi-asserted-by":"publisher","first-page":"2018","DOI":"10.1039\/b911852g","article-title":"Sulfones: new reagents in organocatalysis","volume":"39","author":"Alba","year":"2010","journal-title":"Chem. Soc. Rev"},{"issue":"14","key":"2026091109105460100_cit1d","doi-asserted-by":"publisher","first-page":"3552","DOI":"10.1021\/acs.orglett.5b01634","article-title":"Pd(II)-Catalyzed Direct Sulfonylation\nof Unactivated C(sp3)\u2013H Bonds with Sodium Sulfinates","volume":"17","author":"Rao","year":"2015","journal-title":"Org. Lett"},{"issue":"3","key":"2026091109105460100_cit1e","doi-asserted-by":"publisher","first-page":"1001","DOI":"10.1021\/jo102359n","article-title":"Palladium-Catalyzed\nConjugate Addition to Electron-Deficient Alkynes with Benzenesulfinic\nAcid Derived from 1,2-Bis- (phenylsulfonyl)ethane: Selective Synthesis\nof (E)-Vinyl Sulfones","volume":"76","author":"Song","year":"2011","journal-title":"J. Org. Chem"},{"issue":"17","key":"2026091109105460100_cit1f","doi-asserted-by":"publisher","first-page":"2604","DOI":"10.1039\/C8QO00661J","article-title":"Metal-free deoxygenative sulfonylation of quinoline\nN-oxides with sodium sulfinates via a dual radical coupling process","volume":"5","author":"Xie","year":"2018","journal-title":"Org. Chem. Front"},{"issue":"26","key":"2026091109105460100_cit2a","doi-asserted-by":"publisher","first-page":"9200","DOI":"10.1021\/acs.joc.5c01135","article-title":"Radical Cross-Coupling\nReaction of NPIB Ester with Sodium Sulfinate Salts for the Synthesis\nof Sulfones","volume":"90","author":"Shah","year":"2025","journal-title":"J. Org. Chem"},{"issue":"17","key":"2026091109105460100_cit2b","doi-asserted-by":"publisher","first-page":"6013","DOI":"10.1021\/acs.joc.5c00396","article-title":"Visible-Light-Mediated\nAddition Reactions of Sulfur-Containing Reagents with \u03b1-Trifluoromethyl\nAlkenes","volume":"90","author":"Chen","year":"2025","journal-title":"J. Org. Chem"},{"issue":"4","key":"2026091109105460100_cit2c","doi-asserted-by":"publisher","first-page":"327","DOI":"10.1038\/s41557-021-00668-4","article-title":"Asymmetric, visible\nlight-mediated radical sulfinyl-Smiles rearrangement to access all-carbon\nquaternary stereocentres","volume":"13","author":"Hervieu","year":"2021","journal-title":"Nat. Chem"},{"issue":"3","key":"2026091109105460100_cit3a","doi-asserted-by":"publisher","first-page":"751","DOI":"10.1021\/acs.orglett.0c03973","article-title":"Copper-Catalyzed\nRadical Aryl Migration\nApproach for the Preparation of Cyanoalkylsulfonylated Oxindoles\/Cyanoalkyl\nAmides","volume":"23","author":"Li","year":"2021","journal-title":"Org. Lett"},{"issue":"51","key":"2026091109105460100_cit3b","doi-asserted-by":"publisher","first-page":"9207","DOI":"10.1021\/acs.orglett.3c03777","article-title":"Simultaneous Preparation\nof Sulfides\/Selenides and Sulfones via Synergistic Nickel-Catalyzed\nReductive Coupling and SN2 Reaction","volume":"25","author":"Cao","year":"2023","journal-title":"Org. Lett"},{"issue":"34","key":"2026091109105460100_cit4a","doi-asserted-by":"publisher","first-page":"9393","DOI":"10.1021\/acs.orglett.5c02666","article-title":"Photocatalytic\nSmiles Rearrangement at Remote C(sp3)\u2013H Bonds","volume":"27","author":"Pal","year":"2025","journal-title":"Org. Lett"},{"issue":"11","key":"2026091109105460100_cit4b","doi-asserted-by":"publisher","first-page":"6774","DOI":"10.1039\/D4GC00186A","article-title":"A radical Smiles rearrangement difunctionalization\nof activated alkenes via desulfonylation and insertion of sulfur dioxide\nrelay strategy","volume":"26","author":"Tian","year":"2024","journal-title":"Green Chem"},{"issue":"81","key":"2026091109105460100_cit4c","doi-asserted-by":"publisher","first-page":"11568","DOI":"10.1039\/D4CC03924F","article-title":"Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones\nvia SO2 insertion\/Smiles rearrangement","volume":"60","author":"Tian","year":"2024","journal-title":"Chem.\nCommun"},{"issue":"12","key":"2026091109105460100_cit5a","doi-asserted-by":"publisher","first-page":"3432","DOI":"10.1021\/jm051122a","article-title":"Structure-based design of spiro-oxindoles\nas potent, specific small-molecule inhibitors of the MDM2\u2013p\n53 interaction","volume":"49","author":"Ding","year":"2006","journal-title":"J. Med. Chem"},{"issue":"24","key":"2026091109105460100_cit5b","doi-asserted-by":"publisher","first-page":"4527","DOI":"10.1002\/ejoc.201000643","article-title":"3-Alkenyl-oxindoles: natural products,\npharmaceuticals, and recent synthetic advances in tandem\/telescoped\napproaches","volume":"2010","author":"Millemaggi","year":"2010","journal-title":"Eur. J. Org. Chem"},{"issue":"6","key":"2026091109105460100_cit5c","doi-asserted-by":"publisher","first-page":"382","DOI":"10.1021\/acsinfecdis.6b00041","article-title":"Therapeutic potential of spirooxindoles\nas antiviral agents","volume":"2","author":"Ye","year":"2016","journal-title":"ACS Infect. Dis"},{"issue":"6","key":"2026091109105460100_cit5d","doi-asserted-by":"publisher","first-page":"1443","DOI":"10.1021\/acs.accounts.8b00097","article-title":"Development of Synthetic Methodologies via Catalytic Enantioselec-\ntive Synthesis of 3,3-Disubstituted Oxindoles","volume":"51","author":"Cao","year":"2018","journal-title":"Acc. Chem. Res"},{"issue":"39","key":"2026091109105460100_cit6a","doi-asserted-by":"publisher","first-page":"12970","DOI":"10.1002\/chem.201302139","article-title":"Copper-catalyzed\noxidative benzylarylation of acrylamides by benzylic C\u2013H bond\nFunctionalization for the synthesis of oxindoles","volume":"19","author":"Zhou","year":"2013","journal-title":"Chem. - Eur. J"},{"issue":"92","key":"2026091109105460100_cit6b","doi-asserted-by":"publisher","first-page":"10817","DOI":"10.1039\/c3cc45861j","article-title":"Oxidative 1,2-difunctionalization of activated alkenes with benzylic\nC(sp3)\u2013H bonds and aryl C(sp2)\u2013H\nbonds","volume":"49","author":"Zhou","year":"2013","journal-title":"Chem.Commun"},{"issue":"42","key":"2026091109105460100_cit7a","doi-asserted-by":"publisher","first-page":"14039","DOI":"10.1002\/chem.201302407","article-title":"Visible-light-induced\ntrifluoromethylation\nof N-aryl acrylamides: a Convenient and effective method to synthesize\nCF3-containing oxindoles bearing a quaternary carbon center","volume":"19","author":"Xu","year":"2013","journal-title":"Chem. - Eur. J"},{"issue":"39","key":"2026091109105460100_cit7b","doi-asserted-by":"publisher","first-page":"14480","DOI":"10.1021\/ja403954g","article-title":"Copper-catalyzed one-pot\ntrifluoromethylation\/aryl migration\/desulfonylation and C(sp2)\u2013N\nbond formation of conjugated tosylamides","volume":"135","author":"Kong","year":"2013","journal-title":"J.\nAm. Chem. Soc"},{"issue":"31","key":"2026091109105460100_cit8a","doi-asserted-by":"publisher","first-page":"7985","DOI":"10.1002\/anie.201303550","article-title":"Metal-free\nradical azidoarylation of alkenes: rapid access to oxindoles by cascade\nC\u2013N and C\u2013C bond-forming reactions","volume":"52","author":"Matcha","year":"2013","journal-title":"Angew. Chem., Int. Ed"},{"issue":"16","key":"2026091109105460100_cit8b","doi-asserted-by":"publisher","first-page":"4158","DOI":"10.1021\/ol402138y","article-title":"Silver-catalyzed carboazidation of arylacrylamides","volume":"15","author":"Wei","year":"2013","journal-title":"Org. Lett"},{"issue":"14","key":"2026091109105460100_cit9a","doi-asserted-by":"publisher","first-page":"7343","DOI":"10.1021\/jo401069d","article-title":"Synthesis of sulfonated oxindoles\nby potassium iodide-catalyzed arylsulfonylation\nof activated alkenes with sulfonylhydrazides in water","volume":"78","author":"Li","year":"2013","journal-title":"J. Org. Chem"},{"issue":"6","key":"2026091109105460100_cit9b","doi-asserted-by":"publisher","first-page":"2988","DOI":"10.1039\/C4GC00231H","article-title":"Catalyst-free direct arylsulfonylation\nof N-arylacrylamides with sulfinic acids: a convenient and efficient\nroute to sulfonated oxindoles","volume":"16","author":"Wei","year":"2014","journal-title":"Green Chem"},{"key":"2026091109105460100_cit10","doi-asserted-by":"publisher","first-page":"10954","DOI":"10.1021\/acs.joc.6c01118","article-title":"Radical-Mediated\nTandem Functional Group Transfer, Desulfonylation, and Cyclization\nReactions: Synthesis of Oxindoles","volume":"91","author":"Shah","year":"2026","journal-title":"J. Org. Chem"},{"issue":"20","key":"2026091109105460100_cit11","doi-asserted-by":"publisher","first-page":"7983","DOI":"10.1039\/D3GC02575F","article-title":"Photoinduced, additive-\nand photosensitizer-free multi-component\nsynthesis of naphthoselenazol-2-amines with air in water","volume":"25","author":"Ji","year":"2023","journal-title":"Green Chem"},{"issue":"24","key":"2026091109105460100_cit12","doi-asserted-by":"publisher","first-page":"12084","DOI":"10.1039\/D4GC04391J","article-title":"Decatungstate-photocatalyzed\ntandem\nacylation\/cyclization\/self-hydrogenation of isocyanides with aldehydes\nto hydroxyalkylated N-heteroarenes via multiple hydrogen atom transfer","volume":"26","author":"Ji","year":"2024","journal-title":"Green Chem"},{"issue":"2","key":"2026091109105460100_cit13","doi-asserted-by":"publisher","first-page":"110167","DOI":"10.1016\/j.cclet.2024.110167","article-title":"Visible-light-induced\nring-opening cross-coupling of cycloalcohols with vinylazaarenes and\nenones via \u03b2-C-C scission enabled by proton-coupled electron\ntransfer","volume":"36","author":"Zhang","year":"2025","journal-title":"Chin. Chem. Lett"},{"issue":"2","key":"2026091109105460100_cit14","doi-asserted-by":"publisher","first-page":"109107","DOI":"10.1016\/j.cclet.2023.109107","article-title":"Additive-free\nsynthesis of S-substituted isothioureas via visible-light-induced\nfour-component reaction of \u03b1-diazoesters, aryl isothiocyanates,\namines and cyclic ethers","volume":"35","author":"Lv","year":"2024","journal-title":"Chin. Chem. Lett"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01612","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/36\/12401\/67442611\/acs.joc.6c01612.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/36\/12401\/67442611\/acs.joc.6c01612.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T13:10:59Z","timestamp":1789132259000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/36\/12401\/5332216\/Radical-Mediated-Functional-Group-Migration-and"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,26]]},"references-count":31,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,8,26]]},"published-print":{"date-parts":[[2026,9,11]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01612","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,26]]}}}