Nuraini Vidia A, Falasca Valerio, Wenholz Daniel S, Black David StC, Kumar Naresh
Study Program of Chemistry, Universitas Pendidikan Indonesia Jl. Dr Setiabudhi 229 Bandung 40154 Indonesia
School of Chemistry, University of New South Wales Sydney NSW 2052 Australia
RSC Adv. 2025 Jan 29;15(4):2912-2929. doi: 10.1039/d4ra08704f. eCollection 2025 Jan 23.
In this study, we investigated the ability of -quinone methide (-QM), an electron-poor diene, to undergo inverse electron-demand Diels-Alder (iEDDA) reaction with electron-rich dienophiles, resulting in fused-ring flavonoid systems. In addition, we explored the Michael-type addition using -QM and various nucleophiles, providing access to diarylmethane products. The cycloaddition reactions proceeded in a highly regioselective way, depending on the charge distribution of the reacting partners. Overall, the electron-rich dienophiles or nucleophiles reacted with the intermediate -QM to afford products in reduced to moderate yields. Electron-poor dienophiles or nucleophiles, on the other hand, failed to react with -QM.
在本研究中，我们研究了贫电子二烯对醌甲基化物（-QM）与富电子亲双烯体发生逆电子需求狄尔斯-阿尔德（iEDDA）反应的能力，从而生成稠环类黄酮体系。此外，我们探索了使用-QM和各种亲核试剂进行迈克尔型加成反应，以得到二芳基甲烷产物。环加成反应以高度区域选择性的方式进行，这取决于反应底物的电荷分布。总体而言，富电子亲双烯体或亲核试剂与中间体-QM反应，以低至中等的产率得到产物。另一方面，贫电子亲双烯体或亲核试剂未能与-QM发生反应。
