{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T07:39:14Z","timestamp":1792136354326,"version":"4.4.0"},"reference-count":37,"publisher":"American Chemical Society (ACS)","issue":"30","license":[{"start":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T00:00:00Z","timestamp":1784160000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008848","name":"Elitenetzwerk Bayern","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008848","id-type":"DOI","asserted-by":"publisher"}]},{"name":"German Research Council (DFG)","award":["TRR 325444632635-A2"],"award-info":[{"award-number":["TRR 325444632635-A2"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Alkenes serve as fundamental motifs across natural products and synthetic molecules, yet efficient, mild, and versatile olefination strategies remain in demand. Nitroalkanes, renowned for their broad reactivity as nucleophiles or corresponding radicals, still offer untapped potential in photocatalysis. Here, we report a unified, photocatalyzed generation of \u03b1-nitroalkyl radicals via oxidation of simple, nonprefunctionalized nitronates, followed by addition to another nitronate (formal homo- or cross-coupling) and subsequent double denitration to furnish alkenes. This transformation leverages both the pro-nucleophilic and pro-electrophilic nature of nitroalkanes, challenging the classic McMurry-type coupling protocol. Moreover, the synthetic manifold is scalable and demonstrates its applicability by synthesizing medicinally relevant Combretastatin and lignan-type cores.<\/jats:p>","DOI":"10.1021\/jacs.6c06459","type":"journal-article","created":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T18:30:22Z","timestamp":1784226622000},"page":"31680-31689","source":"Crossref","is-referenced-by-count":4,"title":["Photocatalytic Denitrative\nHomo- and Cross-Coupling\nof Nitroalkanes toward the Synthesis of Alkenes"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-7592-8995","authenticated-orcid":true,"given":"Max","family":"Dietel","sequence":"first","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-2632-303X","authenticated-orcid":true,"given":"Mangish","family":"Ghosh","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hendrik","family":"Paps","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zen","family":"Shimizu","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonas","family":"Scholl","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael Andreas","family":"Gruber","sequence":"additional","affiliation":[{"name":"Universita\u0308tsklinikum Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1430-573X","authenticated-orcid":true,"given":"Oliver","family":"Reiser","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,16]]},"reference":[{"issue":"6","key":"2026080511150838900_cit1","doi-asserted-by":"publisher","first-page":"396","DOI":"10.1007\/s00897010513a","article-title":"Organic Chemistry,\nby J. 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Rev."},{"issue":"6","key":"2026080511150838900_cit6","doi-asserted-by":"publisher","first-page":"717","DOI":"10.3390\/ph15060717","article-title":"The Diverse Biological\nActivity of\nRecently Synthesized Nitro Compounds","volume":"15","author":"Noriega","year":"2022","journal-title":"Pharmaceuticals"},{"key":"2026080511150838900_cit7","doi-asserted-by":"crossref","DOI":"10.1002\/0471224480","volume-title":"The Nitro Group in Organic\nSynthesis","author":"Ono","year":"2001"},{"issue":"7930","key":"2026080511150838900_cit8","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1038\/s41586-022-05211-0","article-title":"Photoexcited nitroarenes\nfor the oxidative cleavage of alkenes","volume":"610","author":"Ruffoni","year":"2022","journal-title":"Nature"},{"issue":"5","key":"2026080511150838900_cit9","doi-asserted-by":"publisher","first-page":"771","DOI":"10.1038\/s41557-023-01429-1","article-title":"Synthesis\nof polysubstituted azepanes by dearomative\nring expansion of nitroarenes","volume":"16","author":"Mykura","year":"2024","journal-title":"Nat. Chem."},{"issue":"12","key":"2026080511150838900_cit10","doi-asserted-by":"publisher","first-page":"4899","DOI":"10.1021\/jacsau.4c00880","article-title":"Selective\nArene Photonitration via Iron-Complex beta-Homolysis","volume":"4","author":"Liu","year":"2024","journal-title":"JACS Au"},{"issue":"4","key":"2026080511150838900_cit11","doi-asserted-by":"publisher","first-page":"3306","DOI":"10.1021\/acscatal.4c07252","article-title":"Iron-Catalyzed Ipso-Nitration\nof Aryl Borides via Visible-Light-Induced \u03b2-Homolysis","volume":"15","author":"Liu","year":"2025","journal-title":"ACS Catal."},{"issue":"16","key":"2026080511150838900_cit12","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202219086","article-title":"Copper(I) Photocatalyzed\nBromonitroalkylation of Olefins: Evidence for Highly Efficient Inner-Sphere\nPathways","volume":"62","author":"Reichle","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"issue":"37","key":"2026080511150838900_cit13","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202509658","article-title":"Copper(II)-Photocatalyzed\nRadical Anellation of Nitroalkanes with Alkenes or Alkynes for the\nSynthesis of Isoxazolines and Isoxazoles","volume":"64","author":"Sardana","year":"2025","journal-title":"Angew.\nChem., Int. Ed."},{"issue":"75","key":"2026080511150838900_cit14","doi-asserted-by":"publisher","first-page":"11014","DOI":"10.1039\/D0CC04821F","article-title":"Redox-regulated divergence\nin photocatalytic addition of alpha-nitro alkyl radicals to styrenes","volume":"56","author":"Tsuchiya","year":"2020","journal-title":"Chem. Commun."},{"issue":"70","key":"2026080511150838900_cit15","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202403654","article-title":"Facile Access to Terminal Nitroalkanes via Anti-Markovnikov\nHydronitration and Hydronitroalkylation of Alkenes Using Photoredox\nCatalysis","volume":"30","author":"Patra","year":"2024","journal-title":"Chem. Eur. J"},{"issue":"8","key":"2026080511150838900_cit16","doi-asserted-by":"publisher","first-page":"1689","DOI":"10.1039\/D4CC06005A","article-title":"Photoredox radical\/polar\ncrossover enables carbo-heterofunctionalization of alkenes: facile\naccess to 1,3-difunctionalized nitro compounds","volume":"61","author":"Patra","year":"2025","journal-title":"Chem. Commun."},{"issue":"16","key":"2026080511150838900_cit17","doi-asserted-by":"publisher","first-page":"3980","DOI":"10.1021\/ja01112a031","article-title":"The Action of Oxidizing Agents on Salts of Nitroalkanes","volume":"75","author":"Shechter","year":"1953","journal-title":"J. Am. Chem. 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Chem."},{"issue":"17","key":"2026080511150838900_cit21","doi-asserted-by":"publisher","first-page":"4316","DOI":"10.1021\/ja00746a051","article-title":"New synthesis of\nolefins","volume":"93","author":"Kornblum","year":"1971","journal-title":"J. Am. Chem. Soc."},{"issue":"24","key":"2026080511150838900_cit22","doi-asserted-by":"publisher","first-page":"9942","DOI":"10.1021\/ja304561c","article-title":"Benzylation\nof nitroalkanes\nusing copper-catalyzed thermal redox catalysis: toward the facile\nC-alkylation of nitroalkanes","volume":"134","author":"Gildner","year":"2012","journal-title":"J. Am. Chem. Soc."},{"issue":"11","key":"2026080511150838900_cit23","doi-asserted-by":"publisher","first-page":"3166","DOI":"10.1021\/ol5014153","article-title":"General route for\npreparing beta-nitrocarbonyl compounds using copper thermal redox\ncatalysis","volume":"16","author":"Gietter","year":"2014","journal-title":"Org. 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Rev."},{"key":"2026080511150838900_cit27","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6c06460","article-title":"Photo-Stitching\nof\nNitroalkanes via Cross-Denitrative Olefination","author":"Mitchell","year":"2026","journal-title":"J. Am. Chem. Soc"},{"key":"2026080511150838900_cit28","unstructured":"Markofsky, S. B.\n          \n          Synthesis of\nNitromethane, US Patent 4,424,385 A, 1982."},{"key":"2026080511150838900_cit29","unstructured":"Jacquinot, B.; Quibel, J.; Mari, R.\n          Process for the Manufacture\nof Nitromethane and Installation, EP 0151074 A2, 1985."},{"issue":"16","key":"2026080511150838900_cit30","doi-asserted-by":"publisher","first-page":"4086","DOI":"10.1021\/ol301713j","article-title":"Palladium-catalyzed\nnitromethylation\nof aryl halides: an orthogonal formylation equivalent","volume":"14","author":"Walvoord","year":"2012","journal-title":"Org. Lett."},{"issue":"6","key":"2026080511150838900_cit31","doi-asserted-by":"publisher","first-page":"1057","DOI":"10.1016\/S0031-9422(00)84404-0","article-title":"New substituted bibenzyls of Frullania\nbrittoniae subsp. Truncatifolia","volume":"15","author":"Asakawa","year":"1976","journal-title":"Phytochemistry"},{"issue":"1","key":"2026080511150838900_cit32","doi-asserted-by":"publisher","first-page":"29","DOI":"10.1016\/j.tiv.2008.09.015","article-title":"Reversal of p-glycoprotein-mediated\nmultidrug resistance by macrocyclic bisbibenzyl derivatives in adriamycin-resistant\nhuman myelogenous leukemia (K562\/A02) cells","volume":"23","author":"Li","year":"2009","journal-title":"Toxicol. In Vitro"},{"issue":"09","key":"2026080511150838900_cit33","doi-asserted-by":"publisher","first-page":"1656","DOI":"10.1055\/s-1999-3570","article-title":"The Synthesis\nof (E) and (Z)-Combretastatins A-4 and a Phenanthrene from Combretum\ncaffrum","volume":"1999","author":"Lawrence","year":"1999","journal-title":"Synthesis"},{"issue":"11","key":"2026080511150838900_cit34","doi-asserted-by":"publisher","first-page":"3033","DOI":"10.1021\/jm0512903","article-title":"Medicinal chemistry of combretastatin\nA4: present and\nfuture directions","volume":"49","author":"Tron","year":"2006","journal-title":"J. Med. Chem."},{"issue":"5","key":"2026080511150838900_cit35","doi-asserted-by":"publisher","first-page":"840","DOI":"10.1021\/om0107035","article-title":"Cross-Metathesis of Vinylsilanes\nwith Allyl Alkyl Ethers Catalyzed by Ruthenium\u2013Carbene Complexes","volume":"21","author":"Kujawa-Welten","year":"2002","journal-title":"Organometallics"},{"issue":"21","key":"2026080511150838900_cit36","doi-asserted-by":"publisher","first-page":"7310","DOI":"10.1021\/jo970877p","article-title":"Effects of Olefin Substitution on the Ring-Closing\nMetathesis of Dienes","volume":"62","author":"Kirkland","year":"1997","journal-title":"J. Org. Chem."},{"issue":"22","key":"2026080511150838900_cit37","doi-asserted-by":"publisher","first-page":"5234","DOI":"10.1021\/jo00257a008","article-title":"Electrochemical\nreduction of vicinal dinitro compounds","volume":"53","author":"Bowyer","year":"1988","journal-title":"J. Org.\nChem."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c06459","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/30\/31680\/65982306\/jacs.6c06459.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/30\/31680\/65982306\/jacs.6c06459.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T15:23:23Z","timestamp":1785943403000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/30\/31680\/5212350\/Photocatalytic-Denitrative-Homo-and-Cross-Coupling"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,16]]},"references-count":37,"journal-issue":{"issue":"30","published-online":{"date-parts":[[2026,7,16]]},"published-print":{"date-parts":[[2026,8,5]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c06459","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,16]]}}}