Citation: Ying Li, Yan-Cheng Hu, Ding-Wei Ji, Wei-Song Zhang, Gu-Cheng He, Yu-Feng Cong, Qing-An Chen. Acid-catalyzed chemoselective C- and O-prenylation of cyclic 1,3-diketones[J]. Chinese Journal of Catalysis, ;2020, 41(9): 1401-1409. doi: 10.1016/S1872-2067(20)63575-6 shu

Acid-catalyzed chemoselective C- and O-prenylation of cyclic 1,3-diketones

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, Liaoning, China

Received Date: 19 January 2020
Revised Date: 27 February 2020

Fund Project: This work was supported by the National Natural Science Foundation of China (21702204, 21801239).

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.
- 5-Chromenones,
- 1,3-Cyclohexanediones,
- O-Prenylation,
- [3+3] Annulation,
- Isoprene,
- Prenol
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