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Here we report a photoinduced electron donor\u2013acceptor complex strategy that enables the sulfurative oxygenation of vinyl bromides with thiols in an EtOH\/H2O medium under metal- and oxidant-free conditions. In this process, thiolate formation triggers EDA complex assembly with vinyl bromides, and light excitation initiates C\u2013Br fragmentation to generate a styrenyl radical that is intercepted through an alcohol\/water relay. The reaction provides \u03b1-thioaryl ketones in up to 81% yield across 32 examples and can be performed on a gram scale. Mechanistic experiments, including radical trapping, EPR, H218O labeling, UV\u2013vis spectroscopy, NMR titration, cyclic voltammetry, and DFT calculations, support a radical-polar pathway involving ethanol trapping, water addition, sulfur transfer, and tautomerization.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03155","type":"journal-article","created":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T14:02:08Z","timestamp":1786716128000},"page":"10848-10852","source":"Crossref","is-referenced-by-count":1,"title":["Alcohol\/Water-Relay\nSulfurative Oxygenation of Vinyl\nBromides Enabled by Photoinduced EDA Complexes"],"prefix":"10.1021","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2713-8080","authenticated-orcid":true,"given":"Indrajit","family":"Karmakar","sequence":"first","affiliation":[{"name":"National Chung Hsing University , , ,","place":["Taichung, Taiwan (R.O.C.), 40227"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ling-You","family":"Chang","sequence":"additional","affiliation":[{"name":"National Chung Hsing University , , ,","place":["Taichung, Taiwan (R.O.C.), 40227"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ci-Yang","family":"Sun","sequence":"additional","affiliation":[{"name":"Soochow University , , No. 70 Linhsi Road , Shihlin District, ,","place":["Taipei, Taiwan (R.O.C.), 111002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9399-8284","authenticated-orcid":true,"given":"Chien-Wei","family":"Chiang","sequence":"additional","affiliation":[{"name":"Soochow University , , No. 70 Linhsi Road , Shihlin District, ,","place":["Taipei, Taiwan (R.O.C.), 111002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0735-5691","authenticated-orcid":true,"given":"Chin-Fa","family":"Lee","sequence":"additional","affiliation":[{"name":"National Chung Hsing University , , ,","place":["Taichung, Taiwan (R.O.C.), 40227"]},{"name":"National Chung Hsing University , , ,","place":["Taichung, Taiwan (R.O.C.), 40227"]},{"name":"National Chung Hsing University , , ,","place":["Taichung, Taiwan (R.O.C.), 40227"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,14]]},"reference":[{"key":"2026090200194605000_cit1a","volume-title":"The Chemistry\nof Organic Sulfur Compounds","author":"Kharasch","year":"1996"},{"key":"2026090200194605000_cit1b","volume-title":"An Introduction to Organosulfur Chemistry","author":"Cremlyn","year":"1996"},{"key":"2026090200194605000_cit2a","doi-asserted-by":"publisher","first-page":"920","DOI":"10.1021\/np3000443","article-title":"Cytotoxic metabolites from the antarctic\npsychrophilic\nfungus oidiodendron truncatum","volume":"75","author":"Li","year":"2012","journal-title":"J. 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U.S.A."},{"key":"2026090200194605000_cit4","doi-asserted-by":"publisher","first-page":"2309","DOI":"10.1021\/np200563x","article-title":"Glionitrin B, a\ncancer invasion inhibitory diketopiperazine\nproduced by microbial coculture","volume":"74","author":"Park","year":"2011","journal-title":"J. Nat. Prod."},{"key":"2026090200194605000_cit5","doi-asserted-by":"publisher","first-page":"2558","DOI":"10.1002\/adsc.201300566","article-title":"Copper-catalyzed synthesis\nof a-thioaryl carbonyl compounds through\nS-S and C-C bond cleavage","volume":"355","author":"Zou","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"2026090200194605000_cit6","doi-asserted-by":"publisher","first-page":"2159","DOI":"10.1002\/chem.201304111","article-title":"Tandem\nPd\/Au-catalyzed route to \u03b1-sulfenylated\ncarbonyl compounds from terminal propargylic alcohols and thiols","volume":"20","author":"Biswas","year":"2014","journal-title":"Chem. Eur. 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