{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T03:05:59Z","timestamp":1787540759551,"version":"build-2736575974"},"reference-count":102,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2025,12,26]],"date-time":"2025-12-26T00:00:00Z","timestamp":1766707200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,12,26]],"date-time":"2025-12-26T00:00:00Z","timestamp":1766707200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22125104"],"award-info":[{"award-number":["22125104"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021171","name":"Basic and Applied Basic Research Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2024A1515010323"],"award-info":[{"award-number":["2024A1515010323"]}],"id":[{"id":"10.13039\/501100021171","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021171","name":"Basic and Applied Basic Research Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2025A1515011907"],"award-info":[{"award-number":["2025A1515011907"]}],"id":[{"id":"10.13039\/501100021171","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2026,1,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In the field of skeleton editing, the development of catalytic single\u2010atom insertion into five\u2010membered rings is highly desirable and holds significant synthetic value. While numerous transition\u2010metal\u2010catalyzed strategies have been established, organocatalytic single\u2010atom insertions into five\u2010membered rings remain scarce due to persistent challenges such as the development of competent organocatalytic systems and the identification of suitable five\u2010membered heterocyclic substrates. To address this gap, we have developed a novel organoiodine\u2010catalyzed single\u2010oxygen atom insertion reaction employing hydroxyl oxindoles and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010centered nucleophiles such as triazoles, indazoles, and purine derivatives to access a broad range of structurally diverse six\u2010membered\n                    <jats:italic>N<\/jats:italic>\n                    ,\n                    <jats:italic>O<\/jats:italic>\n                    \u2010heterocycles. Control experiments and theoretical calculations provide deep insight into the reaction mechanism and the activation mode underlying this organoiodine\u2010catalyzed transformation. Notably, theoretical studies reveal that hexafluoro\u20102\u2010propanol (HFIP) plays a critical role by forming multiple hydrogen\u2010bonding and C\u2500H\u2022\u2022\u2022\u03c0 interactions with the reactants, thereby facilitating the single\u2010oxygen atom insertion. This work constitutes the first example of organocatalytic oxygen atom insertion in molecular skeletal editing and marks the first use of hydroxyl oxindoles as substrates in this context, enabling skeletal editing of five\u2010membered non\u2010aromatic heterocycles. Moreover, this study presents a successful case of catalytic intermolecular oxidation within organoiodine chemistry, thereby contributing substantially to related research areas.\n                  <\/jats:p>","DOI":"10.1002\/anie.202519764","type":"journal-article","created":{"date-parts":[[2025,12,26]],"date-time":"2025-12-26T14:04:33Z","timestamp":1766757873000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Skeletal Editing of Hydroxyl Oxindoles via Organoiodine\u2010Catalyzed Oxygen Atom Insertion Reaction"],"prefix":"10.1002","volume":"65","author":[{"given":"Yang","family":"Wang","sequence":"first","affiliation":[{"name":"Institute of Functional Heterocycles School of Petrochemical Engineering Changzhou University  Changzhou 213164 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin\u2010Zhi","family":"Zhou","sequence":"additional","affiliation":[{"name":"Institute of Functional Heterocycles School of Petrochemical Engineering Changzhou University  Changzhou 213164 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin\u2010Yan","family":"Ke","sequence":"additional","affiliation":[{"name":"Department of Chemistry Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University  Shantou 515063 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yue","family":"Wang","sequence":"additional","affiliation":[{"name":"Institute of Functional Heterocycles School of Petrochemical Engineering Changzhou University  Changzhou 213164 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shao\u2010Fei","family":"Ni","sequence":"additional","affiliation":[{"name":"Department of Chemistry Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University  Shantou 515063 China"},{"name":"Chemistry and Chemical Engineering Guangdong Laboratory  Shantou 515063 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3922-0708","authenticated-orcid":false,"given":"Feng","family":"Shi","sequence":"additional","affiliation":[{"name":"Institute of Functional Heterocycles School of Petrochemical Engineering Changzhou University  Changzhou 213164 China"},{"name":"School of Chemistry and Materials Science Jiangsu Normal University  Xuzhou 221116 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,12,26]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400628s"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160\u2010022\u201000052\u20101"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.202200182"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c01841"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5c00014"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00846"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00820"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00853"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5c00091"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CS00974F"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO02157F"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00138"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00569"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010024\u201046188\u2010w"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010024\u201001730\u20107"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.5c01324"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00709"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202500336"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adl4755"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c08361"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c06798"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c06287"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09616"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305081"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202305081"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c12119"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202317104"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202317104"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c02012"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/d5cc01777g"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.add1383"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202213041"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202213041"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010022\u201028099\u2010w"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03264"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407384"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202407384"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adp0974"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202505341"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202505341"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.11.210"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b10255"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.1c00285"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010024\u201001468\u20102"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202313807"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202313807"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202401359"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202401359"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010024\u201054379\u20108"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02633"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010024\u201001680\u20100"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202501966"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202501966"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c06139"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.025.202505855"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010023\u201001089\u2010x"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929\u2010024\u201001123\u20106"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c03868"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c06690"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202508379"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202508379"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00602"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-17580-z"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00509"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426\u2010022\u20101471\u20102"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO00515E"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209494"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202209494"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203212"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202203212"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201040491\u20108"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC03746D"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c16062"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202424773"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202424773"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202422951"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202422951"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c14589"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.abg5526"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC01138D"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00837"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100793"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.2c03072"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c04694"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c08640"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010024\u201048727\u2010x"},{"key":"e_1_2_7_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202403957"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202403957"},{"key":"e_1_2_7_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00549"},{"key":"e_1_2_7_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00465"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426\u2010023\u20101927\u20103"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426\u2010024\u20102472\u20102"},{"key":"e_1_2_7_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202507804"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202507804"},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010025\u201062035\u2010y"},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03224"},{"key":"e_1_2_7_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02929"},{"key":"e_1_2_7_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02167"},{"key":"e_1_2_7_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202400852"},{"key":"e_1_2_7_85_1","unstructured":"Deposition Numbers 2450108 (4aa) 2450417 (4ia) 2503198 (4ua) 2503692 (4b\u2032a) 2450110 (4f\u2032a) 2503195 (1\u2032da) 2503194 (1\u2032aa) 2450109 (6) 2450111 (8) and 2503197 (9) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structure service."},{"key":"e_1_2_7_86_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2021.153601"},{"key":"e_1_2_7_87_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202203879"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202519764","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202519764","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202519764","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,5,19]],"date-time":"2026-05-19T16:34:53Z","timestamp":1779208493000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202519764"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,26]]},"references-count":102,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2026,1,28]]}},"alternative-id":["10.1002\/anie.202519764"],"URL":"https:\/\/doi.org\/10.1002\/anie.202519764","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,12,26]]},"assertion":[{"value":"2025-09-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-12-08","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-12-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e19764"}}