BF3·OEt2-AgSCF3 Mediated Trifluoromethylthiolation/Cascade Cyclization of Propynols: Synthesis of 4-((Trifluoromethyl)thio)-2H-chromene and 4-((Trifluoromethyl)thio)-1,2-dihydroquinoline Derivatives | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

3217400

Reference Type

Journal Article

Title

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

Author(s)

Qiu, YF; Song, XR; Li, M; Zhu, XY; Wang, AQ; Yang, F; Han, YP; Zhang, HR; Jin, DP; Li, YX; Liang, YM

Year

2016

Is Peer Reviewed?

Journal

Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052

Volume

Issue

Page Numbers

1514-1517

Language

English

PMID

26974231

DOI

10.1021/acs.orglett.6b00065

Abstract

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.