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BF3·OEt2‑AgSCF3 Mediated Trifluoro­methyl­thiolation/Cascade Cyclization of Propynols: Synthesis of 4‑((Trifluoro­methyl)­thio)‑2H‑chromene and 4‑((Trifluoro­methyl)­thio)-1,2-dihydro­quinoline Derivatives

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posted on 2016-03-14, 18:04 authored by Yi-Feng Qiu, Xian-Rong Song, Ming Li, Xin-Yu Zhu, An-Qi Wang, Fang Yang, Ya-Ping Han, Heng-Rui Zhang, Dong-Po Jin, Ying-Xiu Li, Yong-Min Liang
A BF3·OEt2–AgSCF3 mediated direct trifluoro­methyl­thiolation/cascade cyclization of propynols involving the SCF3 anion nucleophilic pathway is developed. This protocol also provides an opportunity to construct valuable trifluoromethylthio-substituted 2H-chromene and 1,2-dihydroquinoline systems with high efficiency under mild conditions. Additionally, the developed BF3·OEt2–AgSCF3 reaction system could be scaled up to gram quantities in a satisfactory yield without inert gas protection.

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