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Herein, we report a palladium\u2010catalyzed radical annulation of \u03b1\u2010iodo\u2010\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diborylalkanes with alkenes, enabling a two\u2010phase approach to these architectures from readily accessible precursors. The key transformation proceeds via a tandem Giese addition\/homolytic aromatic substitution sequence and accommodates a broad range of (hetero)aromatic systems with diverse electronic properties and substitution patterns. Mechanistic experiments are consistent with the intermediacy of\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diboryl carbon\u2010centered radicals, and density functional theory (DFT) calculations support the proposed Pd(I)\/radical catalytic cycle. The retained\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diboryl moiety in the products provides opportunities for diverse downstream functionalization and skeletal diversification, including deborylative cyclization to fused and bridged tricyclic frameworks that are otherwise difficult to obtain. This study establishes a boron\u2010enabled platform for semisaturated scaffold construction and highlights the synthetic potential of \u03b1\u2010iodo\u2010\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diboryl reagents.\n                  <\/jats:p>","DOI":"10.1002\/anie.7256888","type":"journal-article","created":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T07:18:11Z","timestamp":1792826291000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Palladium\u2010Catalyzed Radical Annulation of \u03b1\u2010Iodo\u2010\n                    <i>gem<\/i>\n                    \u2010Diborylalkanes with Alkenes: A Facile Approach to Semisaturated Cyclic Scaffolds"],"prefix":"10.1002","author":[{"given":"Xiao\u2010Yu","family":"Xie","sequence":"first","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and 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