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However, the unclear origin of scission selectivity hinders the rational design of new transformations using these elementary steps. Here we report a comprehensive study of phosphoranyl radical scission mechanisms for sulfonamide nucleophiles. Using a combination of experimental, computational, and machine-learning-driven strategies, the primary factors influencing selectivity in these transformations were uncovered. Computational and experimental studies revealed an unexpected Curtin\u2013Hammett scenario and demonstrated the impact of reaction stoichiometry on selectivity outcomes. Statistical modeling enabled selectivity prediction via an interpretable linear regression model, which revealed that small, electron-poor phosphines favor \u03b2-scission. Taken together, these studies expose the interplay of reaction conditions, phosphine properties, and alkene properties, which can be used to control selectivity in phosphoranyl-radical-mediated reactions of sulfonamides. These insights were harnessed to develop a photoredox-catalyzed phosphine-mediated hydrosulfonylation reaction of alkenes, the development of which makes primary sulfonamides the first example of a nucleophile with switchable scission selectivity controlled only by phosphine and reaction conditions for phosphoranyl-radical-mediated reactions.<\/jats:p>","DOI":"10.1021\/jacs.6c11233","type":"journal-article","created":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T22:56:45Z","timestamp":1787439405000},"page":"37121-37133","source":"Crossref","is-referenced-by-count":1,"title":["Origin of Scission\nSelectivity for Phosphoranyl Radicals\nin Photoredox Catalysis"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7482-3144","authenticated-orcid":true,"given":"Emily R.","family":"Wearing","sequence":"first","affiliation":[{"name":"University of California , , , ,","place":["Los Angeles, California, United States, 90095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Niharika","family":"Prakash Kaushik","sequence":"additional","affiliation":[{"name":"University of Utah , , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-8402-6870","authenticated-orcid":true,"given":"Samuel T.","family":"Hugie","sequence":"additional","affiliation":[{"name":"University of California , , , ,","place":["Los Angeles, California, United States, 90095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5746-8830","authenticated-orcid":true,"given":"Matthew S.","family":"Sigman","sequence":"additional","affiliation":[{"name":"University of Utah , , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6641-0833","authenticated-orcid":true,"given":"Abigail G.","family":"Doyle","sequence":"additional","affiliation":[{"name":"University of California , , , ,","place":["Los Angeles, California, United States, 90095"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,21]]},"reference":[{"issue":"17","key":"2026090312085361300_cit1","doi-asserted-by":"publisher","first-page":"9790","DOI":"10.1021\/acs.chemrev.0c00278","article-title":"Generation of Alkyl Radicals: From the Tyranny of Tin\nto the Photon Democracy","volume":"120","author":"Crespi","year":"2020","journal-title":"Chem. 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Chem."},{"issue":"10","key":"2026090312085361300_cit28","doi-asserted-by":"publisher","first-page":"5814","DOI":"10.1021\/acscatal.0c00690","article-title":"Photocatalytic\nDeoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations\nand Synthetic Applications","volume":"10","author":"Clarke","year":"2020","journal-title":"ACS Catal."},{"issue":"43","key":"2026090312085361300_cit29","doi-asserted-by":"publisher","first-page":"18331","DOI":"10.1021\/jacs.1c09484","article-title":"Phosphine\/Photoredox Catalyzed Anti-Markovnikov\nHydroamination of Olefins with Primary Sulfonamides via \u03b1-Scission\nfrom Phosphoranyl Radicals","volume":"143","author":"Chinn","year":"2021","journal-title":"J. Am. Chem. Soc."},{"issue":"26","key":"2026090312085361300_cit30","doi-asserted-by":"publisher","first-page":"14510","DOI":"10.1021\/jacs.3c04112","article-title":"Unlocking the Potential of \u03b2-Fragmentation\nof Aminophosphoranyl Radicals for Sulfonyl Radical Reactions","volume":"145","author":"Kim","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"2026090312085361300_cit31","doi-asserted-by":"publisher","first-page":"312","DOI":"10.1002\/anie.201811522","article-title":"Deoxygenative Deuteration\nof Carboxylic Acids with D2O","volume":"58","author":"Zhang","year":"2019","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"31","key":"2026090312085361300_cit32","doi-asserted-by":"publisher","first-page":"5994","DOI":"10.1039\/D0OB01083A","article-title":"Recent Advances\nin PIII-Assisted Deoxygenative Reactions under Photochemical or Electrochemical\nConditions","volume":"18","author":"Shao","year":"2020","journal-title":"Org. Biomol. 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Chem."},{"issue":"7","key":"2026090312085361300_cit39","doi-asserted-by":"publisher","first-page":"2286","DOI":"10.1021\/ja00788a031","article-title":"Free-Radical\nChemistry of Organophosphorus Compounds. III.. Alpha. vs.. Beta. Scission\nin Reactions of Alkoxy and Thiyl Radicals with Trivalent Organophosphorus\nDerivatives","volume":"95","author":"Bentrude","year":"1973","journal-title":"J. Am. Chem. Soc."},{"issue":"10","key":"2026090312085361300_cit40","doi-asserted-by":"publisher","first-page":"1101","DOI":"10.1039\/P29740001101","article-title":"Homolytic Organometallic Reactions.\nPart XII. An Electron Spin Resonance Study of the \u03b1-Scission\nof Alkoxyalkylphosphoranyl Radicals in Solution","volume":"2","author":"Davies","year":"1974","journal-title":"J. Chem. 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