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

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

doi:10.1021/acs.orglett.6b00065

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

Org Lett. 2016 Apr 1;18(7):1514-7. doi: 10.1021/acs.orglett.6b00065. Epub 2016 Mar 14.

Authors

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, People's Republic of China.
² Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University , Nanchang, People's Republic of China.
³ College of Science, Northwest A&F University , 3 Taicheng Road, Yangling, People's Republic of China.

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.

Publication types

Research Support, Non-U.S. Gov't