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Here, we report a metal\u2010 and light\u2010free radical sulfinamidation of alkenes that proceeds through a radical chain mechanism enabled by a proton\u2010coupled electron transfer\u2013hydrogen atom transfer (PCET\u2013HAT) relay, initiated by trace amounts of oxygen. This transformation operates under operationally simple conditions, enabling rapid access to structurally diverse sulfinamides with broad substrate scope and excellent functional group tolerance. The synthetic utility of this strategy is demonstrated by the late\u2010stage functionalization of complex natural products and drug molecules. Mechanistic investigations combining experimental studies and density functional theory calculations reveal a PCET\u2010initiated radical chain process in which a HAT event relays reactivity to generate sulfinyl radicals, accounting for the high efficiency and selectivity of the reaction. This work establishes a mechanistically distinct platform for alkene sulfinamidation and highlights the potential of radical chain processes enabled by PCET\u2013HAT relays in synthetic chemistry.<\/jats:p>","DOI":"10.1002\/anie.2451961","type":"journal-article","created":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T10:26:56Z","timestamp":1788258416000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Radical Sulfinamidation of Alkenes Enabled by a PCET\u2013HAT Relay"],"prefix":"10.1002","author":[{"given":"Fen\u2010Ya","family":"Xiong","sequence":"first","affiliation":[{"name":"Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of Education College of Chemistry, Central China Normal University  Wuhan P. R. 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China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1758-3914","authenticated-orcid":false,"given":"Zhihan","family":"Zhang","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of Education College of Chemistry, Central China Normal University  Wuhan P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen\u2010Jing","family":"Xiao","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of Education College of Chemistry, Central China Normal University  Wuhan P. R. China"},{"name":"Wuhan Institute of Photochemistry and Technology  Wuhan Hubei P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2177-4729","authenticated-orcid":false,"given":"Liang\u2010Qiu","family":"Lu","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of Education College of Chemistry, Central China Normal University  Wuhan P. R. China"},{"name":"Wuhan Institute of Photochemistry and Technology  Wuhan Hubei P. R. China"},{"name":"School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang P. R. 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