Ying Li, Yancheng Hu, Ding‐Wei Ji
Sep 1, 2020
Citations
0
Influential Citations
6
Citations
Journal
Chinese Journal of Catalysis
Abstract
Abstract The chemoselective C- and O-prenylation of cyclic 1,3-diketones was achieved by tuning the prenyl source and catalyst. In the presence of the solid acid Nafion, the coupling of 1,3-cyclohexanediones with isoprene gave C-prenylated 5-chromenones. Alternatively, using prenol as the substrate with the Lewis acid AlCl3 as the catalyst resulted in the exclusive O-prenylation of 1,3-cyclohexanediones. Notably, the resulting products could easily undergo aromatization to deliver prenylated resorcinols that are otherwise difficult to prepare. Our methodology is highly selective, atom-economical, operationally simple, easily scalable, and has potential applications throughout organic synthesis.