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Herein, we report that BCB derivatives bearing\n                    <jats:italic>\u03b2<\/jats:italic>\n                    \u2010positioned hydroxyl or tosylamino groups (i.e.,\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010BCB alcohols or amines) undergo an unusual iodine(I)\u2010mediated 4\u2010endo cyclization to afford 2\u2010oxabicyclo[2.1.1]hexanes and 2\u2010azabicyclo[2.1.1]hexanes (BCHs). This strategy addresses a major limitation of prior BCHs synthesis, which typically require substrates tethered to carbonyl groups or aromatic rings to enable electronic polarization or photo\u2010excitability. By circumventing this requirement, our method significantly broadens the range of substituents that can be incorporated into the BCH framework. Additionally, the transformation features practical advantages, including straightforward one\u2010step substrate preparation, mild reaction conditions, and rapid kinetics\u2014often completing within minutes. Mechanistic studies suggest that the 4\u2010endo cyclization proceeds via an iodonium\u2010induced carbocation intermediate, which is intramolecularly trapped by the nucleophilic \u2500OH or \u2500NHTs group.\n                  <\/jats:p>","DOI":"10.1002\/anie.202523632","type":"journal-article","created":{"date-parts":[[2025,12,4]],"date-time":"2025-12-04T12:43:13Z","timestamp":1764852193000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Iodine(I)\u2010Induced Skeletal Rearrangement of \u03b1\u2010Bicyclobutanyl Alcohols and Amines: A Universal Approach to 2\u2010Oxabicyclo[2.1.1]hexanes and 2\u2010Azabicyclo[2.1.1]hexanes"],"prefix":"10.1002","volume":"65","author":[{"given":"Yuchen","family":"Wang","sequence":"first","affiliation":[{"name":"Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University College of Chemistry at Fuzhou University Fuzhou 350108 P.R. 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