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

doi:10.1016/S1872-2067(20)63575-6

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.

Key words: 5-Chromenones, 1,3-Cyclohexanediones, O-Prenylation, [3+3] Annulation, Isoprene, Prenol

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.

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