کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1313855 | 1499344 | 2013 | 8 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction](/preview/png/1313855.png)
• Fluoroalkylated cis-enediynes are prepared via the highly stereoselective addition–elimination reaction.
• The stereoselectivity is approximately (E)/(Z) ≥ 95/5.
• Various cis-enediynes are prepared only in 5 steps.
Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospecifically to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition–elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity.
Various fluoroalkylated cis-enediynes were stereoselectively synthesized only in 5 steps, starting from commercially available polyfluoroalcohols.Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 156, December 2013, Pages 144–151