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While established methods allow for acylation at ortho- or para-positions, selective meta-C\u2013H acylation remains an unsolved problem. Here, we report a mild protocol for meta-C\u2013H acylation of pyridines via redox-neutral temporary dearomatization. The sequence involves tandem cycloadditive dearomatization, synergistic N-heterocyclic carbene (NHC)\/photoredox-catalyzed C\u2013H acylation, and acid-promoted rearomatization. Mechanistic investigations, including experimental studies and density functional theory (DFT) calculations, support a pathway involving the concurrent generation of oxazino-pyridine-derived allylic-type radicals and acyl azolium radicals, followed by their radical\u2013radical cross-coupling.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c02379","type":"journal-article","created":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T09:45:54Z","timestamp":1784195154000},"page":"9647-9653","source":"Crossref","is-referenced-by-count":2,"title":["Selective\n                    <i>meta<\/i>\n                    -C\u2013H Acylation\nof Pyridines through\n                    <i>N<\/i>\n                    -Heterocyclic Carbene\nand Photoredox Dual Catalysis"],"prefix":"10.1021","volume":"28","author":[{"given":"Jiayu","family":"Luo","sequence":"first","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qixin","family":"Li","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mei","family":"Wang","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mingjie","family":"Liu","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mingkai","family":"Yang","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinyu","family":"Gao","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Xiang","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Tan","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7431-2515","authenticated-orcid":true,"given":"Shengdong","family":"Wang","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6521-8946","authenticated-orcid":true,"given":"Zhi","family":"Zhou","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hui","family":"Gao","sequence":"additional","affiliation":[{"name":"Nanfang College Guangzhou , , , ,","place":["Guangzhou, Guangdong, China, 510970"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7936-9326","authenticated-orcid":true,"given":"Wei","family":"Yi","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3366-7592","authenticated-orcid":true,"given":"Zhongyi","family":"Zeng","sequence":"additional","affiliation":[{"name":"Guangzhou Medical University , , , ,","place":["Guangzhou, Guangdong, China, 511436"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,16]]},"reference":[{"issue":"11","key":"2026073109271980000_cit1","doi-asserted-by":"publisher","first-page":"1226","DOI":"10.1002\/pi.2661","article-title":"Polymer Electrolyte Membranes for\nHigh-temperature Fuel Cells Based on Aromatic Polyethers Bearing Pyridine\nUnits","volume":"58","author":"Kallitsis","year":"2009","journal-title":"Polym. Int."},{"key":"2026073109271980000_cit2","doi-asserted-by":"publisher","first-page":"2265","DOI":"10.3762\/bjoc.9.265","article-title":"An Overview\nof the Synthetic Routes to the Best Selling\nDrugs Containing 6-Membered Heterocycles","volume":"9","author":"Baumann","year":"2013","journal-title":"Beilstein\nJ. Org. Chem."},{"issue":"12","key":"2026073109271980000_cit3","doi-asserted-by":"publisher","first-page":"3407","DOI":"10.1021\/ar500112b","article-title":"Pyridine\nCoordination Chemistry for Molecular Assemblies on Surfaces","volume":"47","author":"De Ruiter","year":"2014","journal-title":"Acc. Chem. Res."},{"issue":"24","key":"2026073109271980000_cit4","doi-asserted-by":"publisher","first-page":"10257","DOI":"10.1021\/jm501100b","article-title":"Analysis\nof the Structural Diversity,\nSubstitution Patterns, and Frequency of Nitrogen Heterocycles among\nU.S. FDA Approved Pharmaceuticals","volume":"57","author":"Vitaku","year":"2014","journal-title":"J. Med. 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Synth."},{"issue":"37","key":"2026073109271980000_cit23","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202510385","article-title":"1,4-Dearomatization of Pyridines\nand Quinolines Enabled by the Carbodication Lewis Acid","volume":"64","author":"Huang","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"issue":"1","key":"2026073109271980000_cit24","doi-asserted-by":"publisher","first-page":"36","DOI":"10.1038\/s44160-025-00915-3","article-title":"Direct Regioselective\nC-3 Halogenation of Pyridines","volume":"5","author":"Li","year":"2026","journal-title":"Nat. Synth."},{"issue":"52","key":"2026073109271980000_cit25","doi-asserted-by":"publisher","first-page":"15876","DOI":"10.1002\/anie.201508181","article-title":"Catalytic Electrophilic C\u2013H Silylation of Pyridines\nEnabled by Temporary Dearomatization","volume":"54","author":"Wu\u0308bbolt","year":"2015","journal-title":"Angew.\nChem., Int. 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Soc."},{"issue":"1","key":"2026073109271980000_cit43","doi-asserted-by":"publisher","first-page":"4121","DOI":"10.1038\/s41467-024-48383-1","article-title":"Introduction of the\nDifluoromethyl Group at the Meta- or Para-Position of Pyridines through\nRegioselectivity Switch","volume":"15","author":"Xu","year":"2024","journal-title":"Nat. Commun."},{"issue":"26","key":"2026073109271980000_cit44","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405385","article-title":"Meta-Selective Copper-Catalyzed C\u2013H\nArylation of Pyridines and Isoquinolines through Dearomatized Intermediates","volume":"63","author":"Guo","year":"2024","journal-title":"Angew. Chem., Int. 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