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Herein, we report a modular electrochemical strategy for the direct dehydroxylative alkylation of tertiary alcohols via a polar\u2010to\u2010radical transduction mechanism. This unified activation platform enables C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2500C(sp\n                    <jats:sup>3<\/jats:sup>\n                    ) bond formation with electron\u2010deficient alkenes and benzyl chlorides, employing readily available reagents under mild, operationally simple conditions. Key to this transformation is the use of halide\u2010based reagents that mediate Lewis acid\u2010promoted C\u2500OH bond cleavage while enabling subsequent radical generation via cathodic reduction. The method exhibits broad substrate scope, including complex and functionalized tertiary alcohols, diverse Michael acceptors, and sterically hindered coupling partners. It is further applicable to the late\u2010stage modification of bioactive molecules and scalable synthesis. Mechanistic studies support the involvement of both carbocation and carbon radical intermediates, validating the effectiveness of this dual\u2010mode strategy. This work provides a general and practical approach to quaternary carbon construction from unactivated tertiary alcohols, expanding the synthetic toolbox for 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.202520816","type":"journal-article","created":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T07:18:06Z","timestamp":1762154286000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Quaternary Carbon Centers via Electrochemical Direct Dehydroxylative Alkylation"],"prefix":"10.1002","volume":"65","author":[{"given":"Yue\u2010Ming","family":"Cai","sequence":"first","affiliation":[{"name":"State Key Laboratory of Synergistic Chem\u2010Bio Synthesis, Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory for Molecular 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