区域选择性
化学
催化作用
机制(生物学)
烯丙醇
钌
药物化学
立体化学
组合化学
有机化学
哲学
认识论
作者
Chao Deng,Po Hu,YouJia Wang,Shaowei Wang,Weihua Zhang
出处
期刊:Dalton Transactions
[Royal Society of Chemistry]
日期:2019-01-01
卷期号:48 (25): 9181-9186
被引量:4
摘要
The reaction mechanism of the Ru(ii)-catalyzed regioselective C-H allylation of indoles with allyl alcohols has been studied by density functional theory (DFT) calculations. This reaction mechanism involves five major steps: deprotonation of amide-NH, arene C-H activation, allyl alcohol insertion, β-OH elimination and protonation. Our calculation results indicate that C2-H bond allylation is better than C7-H bond allylation, which can be attributed to the stronger nucleophilicity of C2 compared to C7 in the C-Ru bond insertion of indole substrates. Furthermore, we also suggest that C-Ru bond insertion is more favorable than N-Ru bond insertion, which can be attributed to the different hybridization states of the relevant carbon and nitrogen atoms. Meanwhile, we also illustrate that the substrate cinnamyl alcohol cannot give the desired product due to the steric hindrance of the phenyl ring in cinnamyl alcohol with the indole skeleton.
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