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The switchable nature of the strategy relies on the selective control between radical cyclization and radical cascade cyclization, dictated by the choice of sulfonyl radical source. Under the photocatalytic conditions, selenosulfonates yielded sulfonylated heterocyclic carboxaldehydes, while sodium aryl sulfinates led to the formation of tricyclic benzo\u2010fused seven\u2010membered sulfones. Under blue LED irradiation, selenosulfonates generate sulfonyl and phenylselenyl radicals. The sulfonyl radical adds chemoselectively to the alkene, triggering a 5\u2010exo\u2010dig cyclization to form a vinyl radical, which is trapped by the phenylselenyl radical. Oxygen and EY\u2010Na\u2082 facilitate the conversion of selenosulfonylated intermediates into sulfonylated 4,5\u2010dihydropyrrole\u20103\u2010carboxaldehydes. A range of 4,5\u2010dihydropyrrole\u20103\u2010carboxaldehydes was synthesized using the developed method. Sodium aryl sulfinates, under blue LED irradiation and in the presence of 1,1,1,3,3,3\u2010Hexafluoro\u20102\u2010propanol\u00a0(HFIP)1,1\u2010Diphenylethylene, react with 1,6\u2010enynes to afford tricyclic benzo\u2010fused seven\u2010membered sulfones. Additionally, the tricyclic sulfone can be readily transformed into a unique bicyclic seven\u2010membered sulfone bearing an exocyclic double bond. A variety of control experiments was performed, providing important mechanistic understanding of both steps in the transformation.<\/jats:p>","DOI":"10.1002\/chem.202502052","type":"journal-article","created":{"date-parts":[[2025,7,25]],"date-time":"2025-07-25T07:20:53Z","timestamp":1753428053000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Visible\u2010Light Mediated Divergent Synthesis of Sulfonylated Dihydropyrrole\u20103\u2010Carboxaldehydes and Tricyclic Sulfones via Sulfonyl Radical Source Modulation"],"prefix":"10.1002","volume":"31","author":[{"given":"Mithu","family":"Roy","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Kamrup Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Itu","family":"Mallick","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Kamrup Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sudipta","family":"Siuli","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Kamrup Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anirban","family":"Bera","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Kamrup Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8826-9773","authenticated-orcid":false,"given":"Dipankar","family":"Srimani","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Kamrup Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,25]]},"reference":[{"key":"e_1_2_8_1_1","volume-title":"Advanced free radical reactions for organic synthesis","author":"Togo H.","year":"2004"},{"key":"e_1_2_8_2_1","volume-title":"Free radical chain reaction in organic synthesis","author":"Motherwell W. 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