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Despite the inherent appeal of constructing these motifs through the direct addition of fluoroalcohols across alkenes, the profound inductive withdrawal exerted by the fluorine atoms engenders a formidable electronic barrier: it drastically suppresses oxygen nucleophilicity, pushes oxidation potentials to prohibitive levels, and renders the \u03b1\u2011C\u2500H bonds kinetically inert. Here, we report a cooperative iron\/disulfide photocatalytic framework that transcends this electronic recalcitrance through an exogenously controlled divergent strategy. By harnessing a photoinduced alkoxide to iron charge transfer (Fe\u2010LMCT) process, this platform bypasses traditional redox limitations to generate reactive fluoroalkoxy radicals from unactivated substrates. We further uncover a concentration\u2010dependent pathway regulated by DMSO: while bulk DMSO promotes a low\u2010barrier 1,2\u2010hydrogen atom transfer (HAT) of the transient fluoroalkoxy radicals to access \u03b1\u2010hydroxyfluoroalkyl radical reactivity, this facilitation is insufficient at additive\u2010level concentrations, thereby prioritizing direct\n                    <jats:italic>O<\/jats:italic>\n                    \u2010centered radical reactivity. This platform provides a robust gateway to structurally complex fluorinated architectures and establishes a blueprint for orchestrating the reactivity of high\u2010energy radical intermediates through external chemical cues.\n                  <\/jats:p>","DOI":"10.1002\/anie.5041475","type":"journal-article","created":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T06:41:55Z","timestamp":1789540915000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["DMSO\u2010Modulated Divergent Fluoroalcohol Addition to Alkenes via Cooperative Iron\/Disulfide Photocatalysis"],"prefix":"10.1002","author":[{"given":"Huaixuan","family":"Guo","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Sciences Shanghai University  Shanghai P. R. 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