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Herein, we report a sacrificial\u2010anode\u2010enabled electroreductive cross\u2010coupling of simple unsaturated carboxylates with unactivated alkyl halides. Aryl, alkenyl, and alkynyl carboxylates are readily incorporated, affording methylene\u2010bridged alkylarenes together with allylic and propargylic C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2010rich frameworks under mild conditions. Mechanistic studies support independent single\u2010electron reduction of both electrophilic partners, followed by radical\u2010radical coupling, alkoxide elimination, and cathodic deoxygenation via a Clemmensen\u2010like reduction pathway. This work establishes unsaturated carboxylates as a new class of alkylating reagents for electroreductive C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2500C(sp\n                    <jats:sup>3<\/jats:sup>\n                    ) bond formation.\n                  <\/jats:p>","DOI":"10.1002\/anie.6256116","type":"journal-article","created":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T10:30:21Z","timestamp":1791109821000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Unsaturated Carboxylates as Electrophilic Synthons for Transition\u2010Metal\u2010Catalyst\u2010Free Electroreductive Deoxygenative Coupling"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-7675-7513","authenticated-orcid":false,"given":"Jianyou","family":"Zhao","sequence":"first","affiliation":[{"name":"Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, College of Pharmacy Nanjing University of Chinese Medicine  Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiaoyang","family":"Liu","sequence":"additional","affiliation":[{"name":"Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, College of Pharmacy Nanjing University of Chinese Medicine  Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zi\u2010Ao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, College of Pharmacy Nanjing University of Chinese Medicine  Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhihui","family":"Sun","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Frontier Interdisciplinary Science Research Center Nanjing University  Nanjing Jiangsu 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