2-酰基苯甲酸酯与α,β-不饱和羰基化合物的电还原偶联：产物选择性的密度泛函理论研究
Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity.
作者信息
Kise Naoki, Sakurai Toshihiko
机构信息
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan.
出版信息
Beilstein J Org Chem. 2022 Aug 2;18:956-962. doi: 10.3762/bjoc.18.95. eCollection 2022.
The electroreductive coupling of 2-acylbenzoates with acrylonitrile in the presence of TMSCl and successive treatment with 1 M HCl gave 2-cyanonaphthalen-1-ols or 3-(3-cyanoethyl)phthalides. On the other hand, the reaction of 2-acylbenzoates with methyl vinyl ketone under the same conditions produced 3-(3-oxobutyl)phthalides as the sole products. What determines the product selectivity was studied using DFT calculations.
在四甲基硅氯（TMSCl）存在下，2-酰基苯甲酸酯与丙烯腈进行电还原偶联反应，随后用1 M盐酸处理，得到2-氰基萘-1-醇或3-(3-氰基乙基)苯酞。另一方面，在相同条件下，2-酰基苯甲酸酯与甲基乙烯基酮反应，仅生成3-(3-氧代丁基)苯酞作为产物。使用密度泛函理论（DFT）计算研究了决定产物选择性的因素。
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