Fe(Ⅲ)促进氢自由基引发MBH酯的烯烃加氢异构化反应OA
Fe(Ⅲ)-promoted hydrogen radical-initiated olefin hydroisomerization of MBH acetates
报道了一类Fe(Ⅲ)介导的Morita-Baylis-Hillman(MBH)酯的烯烃加氢异构化反应.该反应利用乙酰丙酮铁[Fe(acac)3]与苯硅烷原位产生的FeH物种与MBH酯进行自由基加成串联反应,合成了19例三取代烯烃,产率中等到良好(33%～77%).基于实验结果和前人的工作,提出了可能的反应机理,其过程涉及FeH物种的原位生成、自由基加成、单电子还原和β-消除等.同时,该反应具有广泛的底物范围,如L-薄荷醇衍生的MBH酯也能顺利地参与该反应.
Fe(Ⅲ)-mediated olefin hydroisomerization of Morita-Baylis-Hillman acetates were repor-ted for the first time.The FeH species were generated in situ by utilizing Fe(acac)3 and phenylsi-lane,which then undergoes radical addition tandem reaction with MBH acetates to synthesize 19 ex-amples of trisubstituted olefins with moderate to good yields(33%—77%).Based on experimental results and previous work,a possible reaction mechanism was proposed,which involves in situ gener-ation of FeH species,radical addition,SET reduction,and β-elimination.Furthermore,this reaction has a wide range of substrates,such as MBH acetate derived from L-menthol,which can participate in the reaction smoothly.
王佳胤;保宇;张名先;张跃;严生虎
常州大学 药学院,江苏 常州 213164常州大学 药学院,江苏 常州 213164常州大学 药学院,江苏 常州 213164常州大学 药学院,江苏 常州 213164常州大学 药学院,江苏 常州 213164
化学化工
Fe(Ⅲ)介导氢自由基MBH酯三取代烯烃
Fe(Ⅲ)-mediatedhydrogen radicalsMBH acetatestrisubstituted olefins
《常州大学学报（自然科学版）》 2025 (5)
19-27,9
常州大学科研启动基金资助项目(ZMF23020007).
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