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

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...

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Published inOrganic letters Vol. 18; no. 7; pp. 1514 - 1517
Main Authors Qiu, Yi-Feng, Song, Xian-Rong, Li, Ming, Zhu, Xin-Yu, Wang, An-Qi, Yang, Fang, Han, Ya-Ping, Zhang, Heng-Rui, Jin, Dong-Po, Li, Ying-Xiu, Liang, Yong-Min
Format Journal Article
LanguageEnglish
Published United States 01.04.2016
Subjects
chemical structure
cyclization reactions
Lewis bases
organic compounds
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Summary: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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ISSN:1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b00065