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Hydrocarbon-Involved Sulfoxide Deoxygenation via Bifunctional Iron-Enabled Electron Buffering and Ligand-to-Metal
Lifang Wang1, Bolin Qiao2, Wenlong He1
1School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024, China.
Abstract:
Sulfur-containing compounds are essential motifs of natural molecules. We herein report a photoinduced iron-catalyzed strategy for efficient sulfoxide deoxygenation under mild conditions. The iron catalyst as the sole additive acts dually: it activates hydrocarbon reductants (also as a solvent) via a ligand-to-metal charge transfer pathway and serves as an "electron buffer" to regulate subsequent electron transfer. This unique mechanism enables a non-chromatography protocol with high efficiency (majority at >95%, up to 99%) and selectivity. The operationally simple method exhibits broad functional group tolerance and wide application in late-stage transformation of drug-derived sulfoxides into bioactive sulfides.
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