ArticleOrganic letters2026
Alcohol/Water-Relay Sulfurative Oxygenation of Vinyl Bromides Enabled by Photoinduced EDA Complexes.
Article in Organic letters, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The direct conversion of vinyl halides into oxygenated sulfur-containing carbonyl compounds using water as the oxygen source remains challenging because it requires coordinated C-halogen activation, radical capture, oxygen incorporation, and C-S bond formation under mild conditions. Here we report a photoinduced electron donor-acceptor 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-Br fragmentation to generate a styrenyl radical that is intercepted through an alcohol/water relay. The reaction provides α-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-vis spectroscopy, NMR titration, cyclic voltammetry, and DFT calculations, support a radical-polar pathway involving ethanol trapping, water addition, sulfur transfer, and tautomerization.
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