Ts2O Promoted Deoxygenative C–H Dithiocarbonation of Quinoline N‑Oxides with Potassium O‑Alkyl Xanthates
A simple, efficient, and practical method for the synthesis of S-quinolyl xanthates was developed via Ts2O-promoted deoxygenative C–H dithiocarbonation of quinoline N-oxides with various potassium O-alkyl xanthates. The reaction performed well under transition-metal-free, base-free, and room-tempera...
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Veröffentlicht in: | Journal of organic chemistry 2024-04, Vol.89 (8), p.5560-5572 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A simple, efficient, and practical method for the synthesis of S-quinolyl xanthates was developed via Ts2O-promoted deoxygenative C–H dithiocarbonation of quinoline N-oxides with various potassium O-alkyl xanthates. The reaction performed well under transition-metal-free, base-free, and room-temperature conditions with wide substrate tolerance. Employing potassium O-tert-butyl xanthate ( t BuOCS2K) as a nucleophile, some valuable quinoline-2-thiones were unexpectedly obtained in a one-pot reaction without any additional base. |
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ISSN: | 0022-3263 1520-6904 1520-6904 |
DOI: | 10.1021/acs.joc.4c00031 |