State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, People's Republic of China.
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University , Nanchang, People's Republic of China.
Org Lett. 2016 Apr 1;18(7):1514-7. doi: 10.1021/acs.orglett.6b00065. Epub 2016 Mar 14.
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.
发展了一种 BF3·OEt2-AgSCF3 介导的丙炔醇的直接三氟甲硫基化/级联环化反应，涉及 SCF3 阴离子亲核途径。该方案还提供了在温和条件下高效构建有价值的三氟甲硫基取代的 2H-色烯和 1,2-二氢喹啉体系的机会。此外，所开发的 BF3·OEt2-AgSCF3 反应体系可以在无需惰性气体保护的情况下扩大到克级规模，并获得令人满意的产率。
