Journal
SYNLETT
Volume 28, Issue 13, Pages 1558-1563Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588728
Keywords
photoredox catalysis; alkyl benzenesulfonates; C-S bond formation; dioxygen; oxidative coupling
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Funding
- National Natural Science Foundation of China [21390400, 21520102003, 21272180, 21302148]
- Hubei Province Natural Science Foundation of China [2013CFA081]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Ministry of Science and Technology of China [2012YQ120060]
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We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O-S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.
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