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Here, we report that enones can serve as diverse alkylidene sources for catalyst\u2010controlled selective C\u2500H alkylation and\/or alkylidenation of various nucleophiles. Treatment of a mixture of ketone (or lactam), enone, and diarylmethanol, with a catalytic amount of Y[N(TMS)<jats:sub>2<\/jats:sub>]<jats:sub>3<\/jats:sub>, gave the corresponding \u03b1\u2010C\u2500H bond alkylation products derived from the alkylidene transfer from enones to ketones\/lactams, whereas the reaction of enones with various C\u2010nucleophiles in the presence of KOH as a catalyst resulted in C\u2500H alkylidenation. Moreover, the application of these strategies for the late\u2010stage modification or structural simplification of some bioactive molecules is also presented. These alkylidene transfer reactions are characterized by operational simplicity, mild reaction conditions, and remarkable catalyst\u2010controlled product outcomes. These results not only demonstrate a significant potential for easily accessible and recyclable enones to serve as versatile alkylidene sources in C\u2500H alkylation and alkylidenation but also provide an attractive and concise method for hydrodealkylidenation of electron\u2010deficient alkenes.<\/jats:p>","DOI":"10.1002\/anie.202502619","type":"journal-article","created":{"date-parts":[[2025,3,14]],"date-time":"2025-03-14T11:15:33Z","timestamp":1741950933000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Versatile C\u2500H Alkylation and Alkylidenation via Catalytic Alkylidene Transfer of Enones"],"prefix":"10.1002","volume":"64","author":[{"given":"Yitu","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Fudan University Shanghai 200438 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoke","family":"Shou","sequence":"additional","affiliation":[{"name":"Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Fudan University Shanghai 200438 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Xu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University College London London WC1E 6BT UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xigeng","family":"Zhou","sequence":"additional","affiliation":[{"name":"Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Fudan University Shanghai 200438 China"},{"name":"State Key Laboratory of Organometallic Chemistry Shanghai 200032 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,3,23]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00182a"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201666"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1607"},{"key":"e_1_2_7_4_1","first-page":"183","volume-title":"Stereoselective Synthesis of Drugs and Natural Products","author":"Kohler M. 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