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Thus, developing new reaction modes is crucial not only for accessing new structural types but also for discovering new mechanisms and reactive intermediates. Herein, we report a diiodohydantoin (DIH)-catalyzed oxidative [3+2] annulation of alkynoates with nitriles that proceeded via a putative Fischer-type iodocarbenoid intermediate. The density functional theory calculations (DFT) supported the idea that the DIH-catalyzed pyridine N-oxide oxidation of alkynoates first generated an \u03b1-iodo-\u03b1,\u03b1\u2032-dicarbonyl carbocation, which resonates as an iodocarbenoid stabilized by iodine lone-pair delocalization. This transient species was then trapped by nitriles to afford pharmaceutically relevant oxazoles with a broad substrate scope and good scalability, and the products were amenable to diverse derivatizations. This work provides experimental and computational evidence for the putative Fischer-type iodocarbenoid, enabling new oxidative transformations of alkynes.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03455","type":"journal-article","created":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T14:02:09Z","timestamp":1790172129000},"page":"12321-12327","source":"Crossref","is-referenced-by-count":0,"title":["Electrophilic\nIodination Reagent-Catalyzed Oxidative\nAnnulation of Alkynoates and Nitriles to Oxazoles via Putative \u03b1,\u03b1\u2032-Dicarbonyl\nIodocarbenoids"],"prefix":"10.1021","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2427-1062","authenticated-orcid":true,"given":"Weilin","family":"Wang","sequence":"first","affiliation":[{"name":"Xi\u2019an Jiaotong University (XJTU) , , ,","place":["Xi\u2019an, P. R. China, 710049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Xu","sequence":"additional","affiliation":[{"name":"Chongqing University , , ,","place":["Chongqing, P. R. China, 401331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junrui","family":"Zhou","sequence":"additional","affiliation":[{"name":"Xi\u2019an Jiaotong University (XJTU) , , ,","place":["Xi\u2019an, P. R. China, 710049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qihang","family":"Yue","sequence":"additional","affiliation":[{"name":"Xi\u2019an Jiaotong University (XJTU) , , ,","place":["Xi\u2019an, P. R. China, 710049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6671-2495","authenticated-orcid":true,"given":"Yongliang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Xi\u2019an Jiaotong University (XJTU) , , ,","place":["Xi\u2019an, P. R. 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Catal."},{"key":"2026100208373124900_cit48","doi-asserted-by":"publisher","first-page":"627","DOI":"10.71267\/mencom.7840","article-title":"Gold-Catalyzed\nO-Transfer Involving Alkynes and Nitriles as a Straightforward Diazo-Free\nRoute to Oxazoles","volume":"35","author":"Dubovtsev","year":"2025","journal-title":"Mendeleev Commun."},{"key":"2026100208373124900_cit49","doi-asserted-by":"publisher","first-page":"2926","DOI":"10.1002\/adsc.201900097","article-title":"Three-Component [2 + 2+1] Gold(I)-Catalyzed\nOxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal\nAlkynes","volume":"361","author":"Dubovtsev","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"2026100208373124900_cit50","doi-asserted-by":"publisher","first-page":"12397","DOI":"10.1021\/acs.joc.5c01570","article-title":"Gold-Catalyzed Single O-Transfer to Internal CF3-Alkynes. Regioselective Synthesis\nof 4-Trifluoromethylated Oxazoles","volume":"90","author":"Mahmedova","year":"2025","journal-title":"J. Org. Chem."},{"key":"2026100208373124900_cit51","doi-asserted-by":"publisher","first-page":"4116","DOI":"10.1021\/acs.orglett.9b01297","article-title":"Gold(I)-Catalyzed Oxidation of Acyl\nAcetylenes to Vicinal Tricarbonyls","volume":"21","author":"Dubovtsev","year":"2019","journal-title":"Org. Lett."},{"key":"2026100208373124900_cit52","doi-asserted-by":"publisher","first-page":"2384","DOI":"10.1002\/ejoc.201900699","article-title":"A Gold-Catalyzed\nAcid-Assisted Regioselective Cyclization\nfor the Synthesis of Polysubstituted Oxazoles","volume":"2020","author":"Wang","year":"2020","journal-title":"Eur. J. Org. 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