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
Hauptverfasser: Zhao, Meng-Yang, Tang, Jia-Jun, Lin, Ying-Jun, Tian, Zhong-Ying, Peng, Sha, Xie, Long-Yong
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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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00031