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However, reports on the cascade annulation of diynes with dinucleophiles are rare and confined to noble-metal catalysts, narrow diyne scopes, and specific reaction types. Herein, we describe a copper-catalyzed formal [5 + 1] annulation of 1,6-diynes with 1H-indole-2-ethanols via vinyl cations, leading to the concise and practical synthesis of tetrahydropyrano indoles. Significantly, this protocol represents the first non-noble-metal-catalyzed annulation of diynes with dinucleophiles.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03340","type":"journal-article","created":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T20:03:51Z","timestamp":1790021031000},"page":"12259-12264","source":"Crossref","is-referenced-by-count":0,"title":["Copper-Catalyzed Formal [5 + 1] Annulation of Diynes\nwith 1\n                    <i>H<\/i>\n                    -Indole-2-ethanols: Construction of\nTetrahydropyrano Indoles"],"prefix":"10.1021","volume":"28","author":[{"given":"Yin-Zhu","family":"Kong","sequence":"first","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chen-Yong","family":"Weng","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fu-Wen","family":"Tan","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7259-494X","authenticated-orcid":true,"given":"Maxim A.","family":"Novikov","sequence":"additional","affiliation":[{"name":"Russian Academy of Sciences , , 47 Leninsky prospekt , ,","place":["Moscow, Russian Federation, 119991"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roman A.","family":"Novikov","sequence":"additional","affiliation":[{"name":"Russian Academy of Sciences , , 47 Leninsky prospekt , ,","place":["Moscow, Russian Federation, 119991"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gongde","family":"Wu","sequence":"additional","affiliation":[{"name":"Nanjing Institute of Technology , , ,","place":["Nanjing, China, 211167"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fu-Shuai","family":"Li","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5551-678X","authenticated-orcid":true,"given":"Bo","family":"Zhou","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]},{"name":"Nankai University , , ,","place":["Tianjin, China, 300071"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3108-2611","authenticated-orcid":true,"given":"Long-Wu","family":"Ye","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]},{"name":"Nanjing Institute of Technology , , ,","place":["Nanjing, China, 211167"]},{"name":"Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , , ,","place":["Shanghai, China, 200032"]},{"name":"School of Chemistry and Chemical Engineering, Nanjing University , , ,","place":["Nanjing, China, 210093"]},{"name":"Henan Normal University , , ,","place":["Xinxiang, China, 453007"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"key":"2026100208374207600_cit1","doi-asserted-by":"publisher","first-page":"23185","DOI":"10.1021\/acs.jmedchem.5c02068","article-title":"Exploiting the 2-(1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic Acid Scaffold to Generate COXTRANs:\nA New Class of Dual Cyclooxygenase Inhibitors-Thromboxane Receptor\nAntagonists","volume":"68","author":"Blua","year":"2025","journal-title":"J. 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Sci."},{"key":"2026100208374207600_cit40","doi-asserted-by":"publisher","first-page":"981","DOI":"10.1038\/s41467-025-67716-2","article-title":"Enantioselective Dearomative Single-Atom\nSkeletal Editing of Benzofurans","volume":"17","author":"Zhu","year":"2026","journal-title":"Nat. Commun."},{"key":"2026100208374207600_cit41","doi-asserted-by":"publisher","first-page":"20817","DOI":"10.1021\/acscatal.5c07241","article-title":"Copper-Catalyzed Intermolecular Asymmetric\nTransformations of Vinyl Cations via [1,2]-Stevens-Type Rearrangement","volume":"15","author":"Ye","year":"2025","journal-title":"ACS Catal."},{"key":"2026100208374207600_cit42","doi-asserted-by":"publisher","first-page":"4107","DOI":"10.1038\/s41467-025-59328-7","article-title":"Ligand-Controlled\nDivergent Asymmetric C(sp3)-H and C(sp3)-O Insertion\nvia Vinyl Cations","volume":"16","author":"Li","year":"2025","journal-title":"Nat. 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