Ligand-Free Copper(I)-Mediated Cross-Coupling Reactions of Organostannanes with Sulfur Electrophiles

The synthesis of aryl thioether through the cross-coupling of C–S bond is a highly attractive area of research due to the prevalence of aryl thioether in bioactive natural products, functional materials, agrochemicals, and pharmaceutically active compounds. Herein, we report a ligand-free Cu­(I) med...

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Veröffentlicht in:Journal of organic chemistry 2020-09, Vol.85 (18), p.11942-11951
Hauptverfasser: Zhu, Feng, Chen, Zhenhao, Walczak, Maciej A
Format: Artikel
Sprache:eng
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Zusammenfassung:The synthesis of aryl thioether through the cross-coupling of C–S bond is a highly attractive area of research due to the prevalence of aryl thioether in bioactive natural products, functional materials, agrochemicals, and pharmaceutically active compounds. Herein, we report a ligand-free Cu­(I) mediated electrophilic thiolation of organostannanes with sulfur electrophiles. A selective transfer of alkyl groups was achieved in reactions with alkyl carbastannatranes affording congested thioethers. This study offers a unified method to access diaryl and aryl alkyl thioethers and was demonstrated in the context of late-stage modifications..
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01399