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 the DFT calculations.
Keywords: 2-acylbenzoates; chlorotrimethylsilane; 3-(3-cyanoethyl)phthalides, 2-cyanonaphthalen-1-ols; electroductive coupling
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Kise, N.; Sakurai, T. Beilstein Arch. 2022, 202238. doi:10.3762/bxiv.2022.38.v1
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