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Herein, we disclose a N-heterocyclic carbene (NHC)-catalyzed redox-neutral formal [4 + 3] annulation of alkynyl aldehydes with 9,10-phenanthrenequinone that enables the efficient construction of fused [1,4] dioxepin-2-one derivatives without the need for external oxidants. Distinct from conventional oxidative NHC catalysis, this transformation exploits the dual role of 9,10-phenanthrenequinone as both an annulation partner and an internal oxidizing mediator, enabling catalyst turnover through a substrate-assisted redox relay process. The protocol features good functional group tolerance and high atom economy, providing a practical strategy for the construction of structurally complex seven-membered O-heterocycles.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c02652","type":"journal-article","created":{"date-parts":[[2026,8,10]],"date-time":"2026-08-10T14:01:52Z","timestamp":1786370512000},"page":"10445-10450","source":"Crossref","is-referenced-by-count":0,"title":["Substrate-Assisted\nRedox-Neutral Formal [4 + 3] Annulation\nof Alkynyl Aldehydes with 9,10-Phenanthrenequinones via N-Heterocyclic\nCarbene Catalysis"],"prefix":"10.1021","volume":"28","author":[{"given":"Fei","family":"Ning","sequence":"first","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sha","family":"Yang","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shupeng","family":"Zhang","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6722-0441","authenticated-orcid":true,"given":"Wenchao","family":"Yang","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3003-6437","authenticated-orcid":true,"given":"Zhichao","family":"Jin","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9173-6608","authenticated-orcid":true,"given":"Jian","family":"Wu","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiguo","family":"Zheng","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shengxin","family":"Guo","sequence":"additional","affiliation":[{"name":"Guizhou University , , ,","place":["Guiyang, China, 550025"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,10]]},"reference":[{"key":"2026082212105341900_cit1a","doi-asserted-by":"publisher","first-page":"3327","DOI":"10.1021\/acs.orglett.3c03877","article-title":"Total synthesis of\nthe sesquiterpene (\u2212)-merrillianin","volume":"26","author":"Shiina","year":"2024","journal-title":"Org.\nLett."},{"key":"2026082212105341900_cit1b","doi-asserted-by":"publisher","first-page":"7647","DOI":"10.1021\/acscatal.7b02302","article-title":"Enantioselective medium-ring\nlactone synthesis through an NHC-catalyzed intramolecular desymmetrization\nof prochiral 1,3-diols","volume":"7","author":"Wu","year":"2017","journal-title":"ACS. 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