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In this work, we introduce a photoinduced, halogen bonding\u2010initiated, metal\u2010free strategy for synthesizing various BCP derivatives. This method involves the generation of nucleophilic \u03b1\u2010aminoalkyl radicals via halogen\u2010bonding adducts. These undergo selective radical addition to [1.1.1]propellane, yielding electrophilic BCP radicals that subsequently participate in polarity\u2010matched additions, culminating in the difunctionalization of bicyclopentane. The versatility and practicality of this metal\u2010free approach are underscored by its broad substrate scope, which includes late\u2010stage functionalization and a series of valuable transformations, all conducted under mild reaction conditions.\n                  <\/jats:p>","DOI":"10.1002\/anie.202411961","type":"journal-article","created":{"date-parts":[[2024,8,28]],"date-time":"2024-08-28T04:47:55Z","timestamp":1724820475000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions"],"prefix":"10.1002","volume":"63","author":[{"given":"Liang","family":"Yi","sequence":"first","affiliation":[{"name":"KAUST Catalysis Center (KCC) King Abdullah University of Science and Technology (KAUST)  23955-6900 Thuwal Saudi 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