Yaragorla Srinivasarao, Shaik Aayesha, Latha Dandugula Sneha
School of Chemistry, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad 500046, India.
J Org Chem. 2025 Apr 4;90(13):4735-4747. doi: 10.1021/acs.joc.5c00326. Epub 2025 Mar 25.
Herein, we report an efficient synthetic protocol for the Friedel-Crafts reaction of imidazo[1,2-]pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In this method, HFIP, besides offering hydrogen bonding with propargyl alcohol, also stabilizes the resultant carbocation, thus forming the product. This method also enables the straightforward synthesis of 1,3-enynes. The current method offers a large substrate diversity with good to excellent yields. We also demonstrated gram-scale synthesis and synthetic modifications.
在此，我们报道了一种在六氟异丙醇（HFIP）中咪唑并[1,2 -]吡啶与炔丙醇进行傅克反应的高效合成方法。值得注意的是，这种傅克烯丙基化反应无需任何额外溶剂或催化剂，既不需要惰性条件也不需要加热。在该方法中，HFIP除了与炔丙醇形成氢键外，还能稳定生成的碳正离子，从而形成产物。该方法还能直接合成1,3 - 烯炔。目前的方法底物多样性高，产率良好至优异。我们还展示了克级规模的合成及合成修饰。
